JPH0696564B2 - α- (ω-hydroxyalkyl) furfuryl alcohol and process for producing the same - Google Patents
α- (ω-hydroxyalkyl) furfuryl alcohol and process for producing the sameInfo
- Publication number
- JPH0696564B2 JPH0696564B2 JP22328986A JP22328986A JPH0696564B2 JP H0696564 B2 JPH0696564 B2 JP H0696564B2 JP 22328986 A JP22328986 A JP 22328986A JP 22328986 A JP22328986 A JP 22328986A JP H0696564 B2 JPH0696564 B2 JP H0696564B2
- Authority
- JP
- Japan
- Prior art keywords
- hydroxyalkyl
- furfuryl alcohol
- reaction
- furan
- producing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 title claims description 36
- 238000000034 method Methods 0.000 title description 2
- 150000002240 furans Chemical class 0.000 claims description 9
- 239000003638 chemical reducing agent Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- -1 lithium aluminum hydrogen Chemical class 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 150000003180 prostaglandins Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KOVPXZDUVJGGFU-UHFFFAOYSA-N 8-methoxy-8-oxooctanoic acid Chemical compound COC(=O)CCCCCCC(O)=O KOVPXZDUVJGGFU-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- YEJWQYJOGFNXRR-UHFFFAOYSA-N methyl 8-(furan-2-yl)-8-oxooctanoate Chemical compound COC(=O)CCCCCCC(=O)C1=CC=CO1 YEJWQYJOGFNXRR-UHFFFAOYSA-N 0.000 description 1
- UOBSVARXACCLLH-UHFFFAOYSA-N monomethyl adipate Chemical compound COC(=O)CCCCC(O)=O UOBSVARXACCLLH-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Furan Compounds (AREA)
Description
【発明の詳細な説明】 本発明は、一般式（Ｉ） （式中、ｎは４〜８の整数を示す） で示されるα−（ω−ヒドロキシアルキル）フルフリル
アルコールおよびその製造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention has the general formula (I) (In the formula, n represents an integer of 4 to 8) and an α- (ω-hydroxyalkyl) furfuryl alcohol and a method for producing the same.
上記一般式（Ｉ）で示されるα−（ω−ヒドロキシアル
キル）フルフリルアルコールは医，農薬中間体、特に以
下に示されるようにプロスタングランディン中間体とし
て有利に利用することができるが、従来、かかるα−
（ω−ヒドロキシアルキル）フルフリルアルコールは全
く知られておらず、本発明者らが初めて合成した新規化
合物である。The α- (ω-hydroxyalkyl) furfuryl alcohol represented by the above general formula (I) can be advantageously used as an intermediate for medicines and agricultural chemicals, particularly as a prostaglandin intermediate as shown below. , Such α-
(Ω-Hydroxyalkyl) furfuryl alcohol is not known at all, and is a novel compound synthesized by the present inventors for the first time.
このようにして得られるプロスタングランディン類は天
然のプロスタグランディン類同族体であり、医薬品とし
て非常に有用である。 The prostaglandins thus obtained are homologues of natural prostaglandins and are very useful as pharmaceuticals.
かかる一般式（Ｉ）で示されるα−（ω−ヒドロキシア
ルキル）フルフリルアルコールは、一般式（II） （式中、Ｒは水素原子または炭素数１〜６のアルキル基
を示し、ｎは４〜８の整数を示す） で示されるフラン誘導体を還元剤を用いて還元すること
により容易に製造することができる。The α- (ω-hydroxyalkyl) furfuryl alcohol represented by the general formula (I) is represented by the general formula (II) (In the formula, R represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and n represents an integer of 4 to 8) and can be easily produced by reducing the furan derivative with a reducing agent. You can
この反応における原料化合物であるフラン誘導体は、た
とえば以下に示されるような、フランを原料としてフリ
ーデルクラフツ反応により合成する方法（米国特許第4,
254,043号明細書）に準じて製造することができる。The furan derivative, which is the starting material compound in this reaction, is synthesized, for example, by the Friedel-Crafts reaction using furan as the starting material as shown below (US Pat.
No. 254,043 specification).
一般式（II）で示されるフラン誘導体の還元反応は、還
元剤の存在下、通常有機溶媒中で行われる。 The reduction reaction of the furan derivative represented by the general formula (II) is usually carried out in an organic solvent in the presence of a reducing agent.
ここで、還元剤としては水素アルミニウムリチウム、水
素化アルミニウム、リチウムトリメトキシアルミニウム
水素化物、リチウムトリ−ｔ−ブトキシアルミニウム水
素化物、ソジウムジ（メトキシエトキシ）アルミニウム
水素化物およびこれらにルイス酸たとえば塩化アルミニ
ウムを添加したもの、水素化ホウ素リチウム、水素化シ
アノホウ素ナトリウム、水素化トリメトキシホウ素ナト
リウムなどの金属水素化物が例示される。Here, as the reducing agent, lithium aluminum hydrogen, aluminum hydride, lithium trimethoxyaluminum hydride, lithium tri-t-butoxyaluminum hydride, sodium di (methoxyethoxy) aluminum hydride and a Lewis acid such as aluminum chloride are added to these. And metal hydrides such as lithium borohydride, sodium cyanoborohydride, and sodium trimethoxyborohydride.
かかる還元剤の使用量は、原料フラン誘導体に対して化
学量論量以上あればよいが、好ましくは化学量論量の２
〜３倍である。The reducing agent may be used in a stoichiometric amount or more with respect to the furan derivative as the raw material, but is preferably 2 stoichiometric amounts.
~ 3 times.
この反応における溶媒としては、ジエチルエーテル、テ
トラヒドロフラン、ジオキサン、1,2−ジメトキシエタ
ンのようなエーテル系溶媒が特に好ましく用いられる。As the solvent in this reaction, ether type solvents such as diethyl ether, tetrahydrofuran, dioxane and 1,2-dimethoxyethane are particularly preferably used.
反応温度は０〜150℃で任意であるが、好ましくは20〜1
00℃である。The reaction temperature is 0 to 150 ° C., but it is preferably 20 to 1
It is 00 ° C.
尚、還元剤として先に例示した金属水素化物以外に、通
常エステル基には作用しないといわれる水素化ホウ素ナ
トリウムを用いることもできる。In addition to the metal hydrides exemplified above as the reducing agent, sodium borohydride, which is said to generally not act on the ester group, can be used.
この場合、原料フラン誘導体に対して過剰量、好ましく
は３〜10倍量の水素化ホウ素ナトリウムを使用し、有機
溶媒好ましくはアルコール性溶媒を用いて還元すること
により原料フラン誘導体中のエステル基も同様に還元さ
れて、目的とするα−（ω−ヒドロキシアルキル）フル
フリルアルコールを得ることができる。In this case, an excess amount, preferably 3 to 10 times, of sodium borohydride with respect to the raw material furan derivative is used, and the ester group in the raw material furan derivative is also reduced by reduction with an organic solvent, preferably an alcoholic solvent. Similarly, the desired α- (ω-hydroxyalkyl) furfuryl alcohol can be obtained by reduction.
この場合の反応温度は50〜150℃で任意であるが、好ま
しくは50〜100℃である。The reaction temperature in this case is 50 to 150 ° C, but is preferably 50 to 100 ° C.
尚、通常の水素化ホウ素ナトリウムによる反応条件で還
元反応を行った場合には、原料フラン誘導体中のカルボ
ニル基のみが還元された化合物が生成するため、本発明
の目的物を得るためには、通常の反応条件よりも反応温
度を高く設定し、反応時間を長くすることが必要であ
る。Incidentally, when the reduction reaction is carried out under the usual reaction conditions with sodium borohydride, a compound in which only the carbonyl group in the furan derivative as a raw material is reduced is produced, and thus in order to obtain the object of the present invention, It is necessary to set the reaction temperature higher than usual reaction conditions and to lengthen the reaction time.
また、水素化ホウ素ナトリウムに塩化アルミニウムある
いはエタンジチオール等を添加することによっても、高
収率で一般式（Ｉ）で示される目的化合物を得ることが
できる。Further, the target compound represented by the general formula (I) can also be obtained in high yield by adding aluminum chloride or ethanedithiol to sodium borohydride.
このような還元反応により得られた反応混合物は、過剰
の未反応還元剤を処理したのち、抽出、分液、濃縮、蒸
留、カラムクロマトグラフィー処理等の操作により、目
的とするα−（ω−ヒドロキシアルキル）フルフリルア
ルコールを分離することができる。The reaction mixture obtained by such a reduction reaction is treated with an excess of unreacted reducing agent and then subjected to operations such as extraction, liquid separation, concentration, distillation, and column chromatography treatment to obtain the desired α- (ω- Hydroxyalkyl) furfuryl alcohol can be separated.
かくして、本発明の方法によれば一般式（II）で示され
るフラン誘導体から一般式（Ｉ）で示されるα−（ω−
ヒドロキシアルキル）フルフリルアルコールが高収率で
得られ、この目的化合物は医薬、農薬等の中間体、特に
プロスタグランディン中間体の原料として有利に用いる
ことができる。Thus, according to the method of the present invention, the furan derivative represented by the general formula (II) is converted into the α- (ω- represented by the general formula (I).
(Hydroxyalkyl) furfuryl alcohol can be obtained in a high yield, and this target compound can be advantageously used as a raw material for intermediates of medicines, agricultural chemicals, etc., especially for prostaglandin intermediates.
以下、実施例により本発明を説明する。Hereinafter, the present invention will be described with reference to examples.
原料製造例１ オーバーヘッドスターラー、温度計を備えた2lフラスコ
にスベリン酸モノメチルエステル122.4g（0.65モル）と
ジクロルメタン400mlを仕込み、これに、無水トリフル
オロ酢酸141.8g（0.68モル）とジクロルメタン100mlの
溶液を30分間で滴下し、さらに室温で30分間攪拌する。
その後フラン260g（3.82モル）とジクロルメタン50mlの
溶液を１時間で滴下し、さらに室温で４時間攪拌する。Raw Material Production Example 1 A 2 l flask equipped with an overhead stirrer and a thermometer was charged with 122.4 g (0.65 mol) of suberic acid monomethyl ester and 400 ml of dichloromethane, to which a solution of 141.8 g (0.68 mol) of trifluoroacetic anhydride and 100 ml of dichloromethane was added. Add dropwise over 30 minutes and stir at room temperature for 30 minutes.
Then, a solution of 260 g (3.82 mol) of furan and 50 ml of dichloromethane was added dropwise over 1 hour, and the mixture was further stirred at room temperature for 4 hours.
反応終了後、反応混合物から減圧下で溶媒を留去する。
留去残にエチルエーテル500mlを加えたのち、有機層を
水洗、次いで７％炭酸水素ナトリウムで洗浄する。After completion of the reaction, the solvent is distilled off from the reaction mixture under reduced pressure.
After adding 500 ml of ethyl ether to the residue, the organic layer is washed with water and then with 7% sodium hydrogen carbonate.
有機層から溶媒を減圧下に留去し、得られたオイル状物
を減圧蒸留することにより、無色オイル状のα−（７−
メトキシカルボニルヘプタノイル）フラン133.3g（収率
86％）を得た。The solvent was distilled off from the organic layer under reduced pressure, and the obtained oily substance was distilled under reduced pressure to obtain a colorless oily α- (7-
Methoxycarbonylheptanoyl) furan 133.3 g (yield
86%).
b.p 136〜139℃/0.2mmHg 原料製造例２ オーバーヘッドスターラー、温度計を備えた１フラス
コにアジピン酸モノメチルエステル96.1g（0.60モル）
とジクロルメタン400mlを仕込み、これに無水トリフル
オロ酢酸131g（0.62モル）とジクロルメタン100mlの溶
液を30分間で滴下し、さらに室温で30分間攪拌する。そ
の後、フラン240g（3.53モル）とジクロルメタン50mlの
溶液を１時間で滴下し、さらに室温で４時間攪拌する。bp 136-139 ℃ / 0.2mmHg Raw material production example 2 96.1g (0.60mol) of adipic acid monomethyl ester in one flask equipped with overhead stirrer and thermometer
And 400 ml of dichloromethane were added thereto, a solution of 131 g (0.62 mol) of trifluoroacetic anhydride and 100 ml of dichloromethane was added dropwise thereto over 30 minutes, and the mixture was further stirred at room temperature for 30 minutes. Then, a solution of 240 g of furan (3.53 mol) and 50 ml of dichloromethane was added dropwise over 1 hour, and the mixture was further stirred at room temperature for 4 hours.
反応終了後、原料製造例１と同様に後処理して無色オイ
ル状のα−（５−メトキシカルボニルペンタノイル）フ
ラン112.3g（収率89％）を得た。After completion of the reaction, post-treatment was carried out in the same manner as in Raw Material Production Example 1 to obtain 112.3 g (yield 89%) of colorless oily α- (5-methoxycarbonylpentanoyl) furan.
b.p 119〜122℃/0.35mmHg 実施例１ オーバーヘッドスターラーおよび温度計を備えた１フ
ラスコに水素化アルミニウムリチウム8.6g（0.23モル）
と乾燥エチルエーテル300mlを仕込み、これに２−（７
−メトキシカルボニルヘプタノイル）フラン35.7g（0.1
5モル）の乾燥エチルエーテル溶液300mlを約３時間で滴
下する。滴下終了後、反応混合物を２時間加熱還流させ
る。その後10℃に冷却し、酢酸エチル10mlを徐々に加
え、過剰の水素化アルミニウムリチウムを分解させたの
ち塩化アンモニウム溶液200mlを加えてよく攪拌する。
不溶物を別ののち、有機層を水洗し、無水硫酸マグネ
シウムにて乾燥する。その後、減圧下に濃縮してα−
（７−ヒドロキシヘプチル）フルフリルアルコール30.9
g（収率97％）を得た。bp 119 to 122 ° C./0.35 mmHg Example 1 Lithium aluminum hydride 8.6 g (0.23 mol) in one flask equipped with an overhead stirrer and thermometer.
And 300 ml of dry ethyl ether were charged, and 2- (7
-Methoxycarbonylheptanoyl) furan 35.7 g (0.1
300 ml of a dry ethyl ether solution (5 mol) are added dropwise in about 3 hours. After the addition is complete, the reaction mixture is heated to reflux for 2 hours. Thereafter, the mixture is cooled to 10 ° C., 10 ml of ethyl acetate is gradually added to decompose excess lithium aluminum hydride, 200 ml of ammonium chloride solution is added, and well stirred.
After removing the insoluble matter, the organic layer is washed with water and dried over anhydrous magnesium sulfate. Then, it is concentrated under reduced pressure and α-
(7-Hydroxyheptyl) furfuryl alcohol 30.9
g (97% yield) was obtained.
▲ｎ25 D▼1.4879 実施例２ 攪拌装置、温度計を装着した４つ口フラスコに水素化ア
ルミニウムリチウム28.5g（0.77モル）および乾燥エー
テル400mlを仕込み、20℃〜還流温度にて２−（５−メ
トキシカルボニルペンタノイル）フラン105.0g（0.5モ
ル）のエーテル溶液200mlを３時間かかって加える。滴
下終了後、さらに２時間還流を続ける。反応終了後、反
応混合物を氷冷下に10％塩化アンモニウム水溶液中へあ
ける。不溶物を別ののち、有機層を水洗し、無水硫酸
マグネシウムにて乾燥する。その後減圧下に濃縮してα
−（５−ヒドロキシペンチル）フルフリルアルコール8
7.4g（収率95％）を得た。<N 25 D > 1.4879 Example 2 28.5 g (0.77 mol) of lithium aluminum hydride and 400 ml of dry ether were placed in a four-necked flask equipped with a stirrer and a thermometer, and 2- (5) at 20 ° C to reflux temperature. 200 ml of an ether solution of 105.0 g (0.5 mol) of -methoxycarbonylpentanoyl) furan is added over 3 hours. After the dropping is completed, the reflux is continued for another 2 hours. After completion of the reaction, the reaction mixture is poured into a 10% ammonium chloride aqueous solution under ice cooling. After removing the insoluble matter, the organic layer is washed with water and dried over anhydrous magnesium sulfate. Then concentrate under reduced pressure and
-(5-Hydroxypentyl) furfuryl alcohol 8
7.4 g (95% yield) was obtained.
▲ｎ25 D▼1.4826▲ n 25 D ▼ 1.4826
Claims (2)
アルコール1. A general formula (In the formula, n represents an integer of 4 to 8) α- (ω-hydroxyalkyl) furfuryl alcohol
を示し、ｎは４〜８の整数を示す） で示されるフラン誘導体を還元剤を用いて還元すること
を特徴とする一般式 （式中、ｎは前記と同じ意味を有する） で示されるα−（ω−ヒドロキシアルキル）フルフリル
アルコールの製造法2. General formula (Wherein, R represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and n represents an integer of 4 to 8), and a furan derivative represented by the formula is reduced using a reducing agent. (In the formula, n has the same meaning as described above.) A method for producing α- (ω-hydroxyalkyl) furfuryl alcohol
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22328986A JPH0696564B2 (en) | 1986-09-20 | 1986-09-20 | α- (ω-hydroxyalkyl) furfuryl alcohol and process for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22328986A JPH0696564B2 (en) | 1986-09-20 | 1986-09-20 | α- (ω-hydroxyalkyl) furfuryl alcohol and process for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6377868A JPS6377868A (en) | 1988-04-08 |
| JPH0696564B2 true JPH0696564B2 (en) | 1994-11-30 |
Family
ID=16795802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22328986A Expired - Lifetime JPH0696564B2 (en) | 1986-09-20 | 1986-09-20 | α- (ω-hydroxyalkyl) furfuryl alcohol and process for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0696564B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2754755B2 (en) * | 1989-06-27 | 1998-05-20 | 住友化学工業株式会社 | Optically active furyl carbinols and their production |
| EP1939191A1 (en) * | 2006-12-28 | 2008-07-02 | Neuropharma S.A. | Furan derivatives, method of synthesis and uses thereof |
| US8350090B1 (en) * | 2011-08-24 | 2013-01-08 | Chirogate International Inc. | Processes for preparing cyclopentenones and cyclopentenones for the synthesis of benzindene prostaglandins |
| CN105646403B (en) * | 2016-03-17 | 2017-11-07 | 浙江工业大学 | A kind of chemical synthesis process of the oxo octanoic acid methyl esters of 8 furans 8 |
-
1986
- 1986-09-20 JP JP22328986A patent/JPH0696564B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6377868A (en) | 1988-04-08 |
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