JPH0148252B2 - - Google Patents
Info
- Publication number
- JPH0148252B2 JPH0148252B2 JP6506081A JP6506081A JPH0148252B2 JP H0148252 B2 JPH0148252 B2 JP H0148252B2 JP 6506081 A JP6506081 A JP 6506081A JP 6506081 A JP6506081 A JP 6506081A JP H0148252 B2 JPH0148252 B2 JP H0148252B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- general formula
- lower alkyl
- alkyl group
- general
- 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
Links
- -1 vinyllithium compound Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052987 metal hydride Inorganic materials 0.000 claims description 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002433 cyclopentenyl group Chemical class C1(=CCCC1)* 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- 150000001941 cyclopentenes Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical group O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- GIZSHQYTTBQKOQ-UHFFFAOYSA-N threo-Syringoylglycerol Chemical compound COC1=CC(C(O)C(O)CO)=CC(OC)=C1O GIZSHQYTTBQKOQ-UHFFFAOYSA-N 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 229960000890 hydrocortisone Drugs 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- ZSBWUNDRDHVNJL-UHFFFAOYSA-N methylcyclopentenone Natural products CC1=CCCC1=O ZSBWUNDRDHVNJL-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229960003387 progesterone Drugs 0.000 description 2
- 239000000186 progesterone Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- PGOLTJPQCISRTO-UHFFFAOYSA-N vinyllithium Chemical class [Li]C=C PGOLTJPQCISRTO-UHFFFAOYSA-N 0.000 description 2
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HWKMEEXAVJYDDF-UHFFFAOYSA-N 1-ethoxy-1-lithioethene Chemical compound [Li]C(=C)OCC HWKMEEXAVJYDDF-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229940107161 cholesterol Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は、シクロペンテン誘導体とその製造法
に関する。
本発明のシクロペンテン誘導体とは、一般式
（）
（式中、R1はC1〜C3の低級アルキル基を表わ
す。）で示されるシクロペンテン類であり、コレ
ステロール、プロゲステロン、ヒドロコルチゾン
などのステロイド医薬およびビタミンD3製造の
中間体として極めて有用である。
たとえば、以下の経路によつて
（式中、Ｒは
The present invention relates to a cyclopentene derivative and a method for producing the same. The cyclopentene derivative of the present invention has the general formula () (In the formula, R 1 represents a C 1 to C 3 lower alkyl group.) These are cyclopentenes represented by the formula (wherein, R 1 represents a C 1 to C 3 lower alkyl group), and are extremely useful as steroid drugs such as cholesterol, progesterone, and hydrocortisone, and as intermediates in the production of vitamin D 3 . For example, by the following route: (In the formula, R is
【式】 又は【formula】 or
【式】を表わす。）
プロゲステロン、ヒドロコルチゾン、ビタミン
D3類が製造され、とくに好ましくは、（5S）−５
−ヒドロキシ−５−（（1R）−１−ヒドロキシエチ
ル）−１−メチル−シクロペンテンからは天然の
光学活性ステロイド類、ビタミンD3類が製造さ
れる。
以下に本発明を詳細に説明する。
本発明の一般式（）で示されるシクロペンテ
ン類は、
（式中、R1はC1〜C3の低級アルキル基を表わす）
５−ヒドロキシ−５−（１−ヒドロキシエチル）
−１−メチル−シクロペンテン、５−ヒドロキシ
−５−（１−ヒドロキシエチル）−１−エチル−シ
クロペンテン及び５−ヒドロキシ−５−（１−ヒ
ドロキシエチル）−１−プロピル−シクロペンテ
ンである。
一般式（）のシクロペンテン誘導体を製造す
るには例えば次の方法による。まず一般式（）
で示される２置換−２−シクロペンテノンに
（式中、R1は一般式（）におけると同義）
一般式（）
CH2＝CLi−Ｏ−R2 （）
（式中、R2は低級アルキル基を表わす。）で示さ
れるビニルリチウム類を作用させて、一般式
（）で示
（式中、R1、R2は一般式（）、（）におけ
ると同義である。）
されるビニルエーテル類を製造する。
ビニルリチウム類としては、たとえば、α−エ
トキシビニルリチウム、α−メトキシビニルリチ
ウム、α−ブトキシビニルリチウムなどの通常公
知のビニルエーテル化試剤であり、好ましくはメ
チルビニルエーテル、エチルビニルエーテル、ブ
チルビニルエーテル等にｎ−ブチルリチウム、Ｓ
−ブチルリチウム、ｔ−ブチルリチウム等の有機
リチウム化合物を作用させて容易に製造される。
その使用量は、一般式（）のシクロペンテノ
ンに対し、当モル以上、好ましくは1.1〜2.0倍モ
ル程度使用される。
シクロペンテノン（）に上記ビニルリチウム
類を作用させるには、通常、ヘキサン、ペンタン
等の飽和炭化水素系、又は、ジエチルエーテル、
テトラヒドロフラン、ジオキサン、メトキシエタ
ン、ジメトキシエタン等のエテル系等の溶媒が使
用される。
反応温度は、−80〜＋10℃、好ましくは−79〜
０℃である。
ビニルエーテル類（）は単離することなく、
溶液状態のまゝでこれに、塩酸、硫酸などの鉱
酸、酢酸、しゆう酸、パラトルエンスルホン酸な
どの有機カルボン酸を含有した希薄水溶液を加え
て短時間で加水分解することができる。
反応温度は−20゜〜40℃、通常、０〜20℃で充
分である。反応時間は、通常、10分程度以下で十
分である。あまり長時間の処理では副生物が生じ
るので好ましくない。
加水分解後、一般式（）で示されるケトン類
を
得る。
次いで、ケトン（）に水素化金属化合物を作
用させ、一般式（）のシクロペンテン類を製造
する。
水素化金属化合物とは水素化ほう素ナトリウ
ム、水素化リチウムアルミニウムなどの通常よく
使用される還元試剤であり、好ましくは水素化ほ
う素ナトリウムである。その使用量はケトン
（）に対し、1.2〜10当量であり、好しくは1.5
〜４当量である。溶媒としては、水素化金属化合
物による還元に用いられる通常の溶媒、例えば、
テトラヒドロフランが挙げられる。反応温度は−
30℃〜室温程度で、好しくは−５〜10℃である。
以下に実施例で更に詳細に説明するが、本発明
はその要旨を超えない限り、以下の実施例により
限定をうけるものではない。
実施例 １
エチルビニルエーテル90mmolを90mlのテトラ
ヒドロフランに溶解する。これにｔ−ブチルリチ
ウム（ペンタン溶液）75mmolをN2雰囲気下に−
10℃〜０℃で滴下し、さらに１時間撹拌する。該
溶液を−78℃に冷し、これにテトラヒドロフラン
50mlに溶解した２−メチルシクロペンテノン
50mmolを、約20分間で撹拌下に滴下する。次に
反応混合物を0.1N塩酸水溶液／テトラヒドロフ
ラン混合液500mlに、冷却下に撹拌しながら注ぎ、
０℃で10分間撹拌する。
テトラヒドロフランをエバボレータで留去し、
塩化メチレンで抽出し、塩化メチレンを留去する
とα−ヒドロキシケトンを液状物で得る。次いで
テトラヒドロフラン20ml／水３mlに上記のケトン
のうち1.9ｇ（13.8mmol）を溶解し、０℃に冷却
する。
これに水素化ほう素ナトリウム669mgを少しづ
つ加え、０℃で約30分間撹拌する。1/10Ｎ塩酸を
加えて撹拌し、過剰の塩酸を重ソウ水で中和し、
次いで塩化メチレンで抽出し、塩化メチレンを濃
縮すると液状物を得る。シリカゲルを充填したカ
ラムに反応物を仕込み25％エーテル／ヘキサンで
分離、留出させる。
（±）５−ヒドロキシ−５−（１−ヒドロキシ
エチル）−１−メチル−シクロペンテンを収率88
％で得た（エリスロ体：80％、スレオ体：８％）。
TLC Rf値＝0.27（エリスロ体）
0.20（スレオ体）
（エーテル／ｎ−ヘキサン＝
４：１）
生成物のNMRスペクトルを第１図（エリスロ
体）及び第２図（スレオ体）に、IRスペクトル
を第３図（エリスロ体）に示した。
なお、中間生成物α−ヒドロキシケトンの
NMRスペクトル及びIRスペクトルをそれぞれ第
４図及び第５図に示した。Represents [formula]. ) progesterone, hydrocortisone, vitamins
D 3 is produced, particularly preferably (5S)-5
Natural optically active steroids, vitamin D 3 , are produced from -hydroxy-5-((1R)-1-hydroxyethyl)-1-methyl-cyclopentene. The present invention will be explained in detail below. The cyclopentenes represented by the general formula () of the present invention are: (In the formula, R 1 represents a C 1 to C 3 lower alkyl group) 5-hydroxy-5-(1-hydroxyethyl)
-1-methyl-cyclopentene, 5-hydroxy-5-(1-hydroxyethyl)-1-ethyl-cyclopentene and 5-hydroxy-5-(1-hydroxyethyl)-1-propyl-cyclopentene. The cyclopentene derivative of general formula () can be produced, for example, by the following method. First, the general formula ()
For the 2-substituted-2-cyclopentenone represented by (In the formula, R 1 has the same meaning as in the general formula ()) Vinyllithium compounds represented by the general formula () CH 2 =CLi-O-R 2 () (In the formula, R 2 represents a lower alkyl group) is expressed by the general formula (). (In the formula, R 1 and R 2 have the same meanings as in the general formulas () and ().) A vinyl ether is produced. Examples of vinyllithiums include commonly known vinyl etherification reagents such as α-ethoxyvinyllithium, α-methoxyvinyllithium, and α-butoxyvinyllithium, preferably n-methyl vinyl ether, ethyl vinyl ether, butyl vinyl ether, etc. Butyl lithium, S
It is easily produced by the action of organic lithium compounds such as -butyllithium and t-butyllithium. The amount to be used is at least one equivalent mole, preferably about 1.1 to 2.0 times the mole of cyclopentenone of general formula (). In order to cause the above vinyllithium to act on cyclopentenone (), a saturated hydrocarbon such as hexane or pentane, or diethyl ether,
Ether solvents such as tetrahydrofuran, dioxane, methoxyethane, and dimethoxyethane are used. The reaction temperature is -80 to +10°C, preferably -79 to +10°C.
It is 0°C. Vinyl ethers () are not isolated,
Hydrolysis can be carried out in a short period of time by adding a dilute aqueous solution containing a mineral acid such as hydrochloric acid or sulfuric acid, or an organic carboxylic acid such as acetic acid, oxalic acid, or para-toluenesulfonic acid to the solution while it is still in the solution state. The reaction temperature is -20° to 40°C, usually 0 to 20°C is sufficient. A reaction time of about 10 minutes or less is usually sufficient. Processing for too long is not preferable because by-products are produced. After hydrolysis, ketones represented by the general formula () are obtain. Next, a metal hydride compound is allowed to act on the ketone () to produce a cyclopentene of the general formula (). The metal hydride compound is a commonly used reducing agent such as sodium borohydride and lithium aluminum hydride, preferably sodium borohydride. The amount used is 1.2 to 10 equivalents, preferably 1.5 equivalents, relative to the ketone ().
~4 equivalents. As the solvent, common solvents used for reduction with metal hydride compounds, for example,
Examples include tetrahydrofuran. The reaction temperature is -
The temperature is about 30°C to room temperature, preferably -5 to 10°C. The present invention will be explained in more detail by way of examples below, but the present invention is not limited by the following examples unless it exceeds the gist thereof. Example 1 90 mmol of ethyl vinyl ether are dissolved in 90 ml of tetrahydrofuran. To this, 75 mmol of t-butyllithium (pentane solution) was added under N2 atmosphere.
Add dropwise at 10°C to 0°C and stir for additional 1 hour. The solution was cooled to -78°C, and tetrahydrofuran was added to it.
2-Methylcyclopentenone dissolved in 50ml
50 mmol are added dropwise under stirring over approximately 20 minutes. Next, the reaction mixture was poured into 500 ml of a 0.1N aqueous hydrochloric acid/tetrahydrofuran mixture while stirring while cooling.
Stir for 10 minutes at 0°C. Tetrahydrofuran is distilled off with an evaporator,
After extraction with methylene chloride and distilling off the methylene chloride, α-hydroxyketone is obtained as a liquid. Next, 1.9 g (13.8 mmol) of the above ketone was dissolved in 20 ml of tetrahydrofuran/3 ml of water and cooled to 0°C. Add 669 mg of sodium borohydride little by little to this and stir at 0°C for about 30 minutes. Add 1/10N hydrochloric acid and stir, neutralize excess hydrochloric acid with hydrogenated sodium chloride solution,
Next, the mixture is extracted with methylene chloride, and the methylene chloride is concentrated to obtain a liquid. The reactants are charged into a column packed with silica gel, separated using 25% ether/hexane, and distilled. (±)5-hydroxy-5-(1-hydroxyethyl)-1-methyl-cyclopentene yield 88
(erythro form: 80%, threo form: 8%). TLC Rf value = 0.27 (erythro form) 0.20 (threo form) (ether/n-hexane =
4:1) The NMR spectra of the product are shown in Figure 1 (erythro form) and Figure 2 (threo form), and the IR spectrum is shown in Figure 3 (erythro form). In addition, the intermediate product α-hydroxyketone
The NMR spectrum and IR spectrum are shown in Figures 4 and 5, respectively.
第１，２及び４図は、実施例の生成物のNMR
スペクトルを示すグラフであり、第３及び５図
は、実施例の生成物のIRスペクトルを示すグラ
フである。
Figures 1, 2 and 4 show NMR of the products of the examples.
Figures 3 and 5 are graphs showing the IR spectra of the products of the examples.
Claims (1)
す。）で示されるシクロペンテン誘導体。 ２ 一般式（） （式中、R1はC1〜C3の低級アルキル基を表わ
す。）で示されるシクロペンテノン類に 一般式（） CH2＝CLi−OR2 （） （式中、R2は低級アルキル基を表わす。）で示さ
れるビニルリチウム類を作用させ、 一般式（） （式中、R1、R2は一般式（）、（）における
と同義とする。）で示されるビニルエーテル類を
得、さらに酸性条件下に加水分解し、 一般式（） （式中、R1は一般式（）におけると同義とす
る。）で示されるケトン類を製造し、該生成物を
水素化金属化合物で還元することを特徴とする 一般式（） （式中、R1は一般式（）におけると同義とす
る。）で表わされるシクロペンテン類の製造法。[Claims] 1 General formula () (In the formula, R 1 represents a C 1 to C 3 lower alkyl group.) A cyclopentene derivative represented by the following formula. 2 General formula () (In the formula, R 1 represents a C 1 to C 3 lower alkyl group.) General formula () CH 2 = CLi−OR 2 () (In the formula, R 2 is a lower alkyl group) (representing a group) is reacted with a vinyllithium compound represented by the general formula (). (In the formula, R 1 and R 2 have the same meanings as in the general formulas () and ().) Vinyl ethers represented by the formula () and () are obtained, and further hydrolyzed under acidic conditions, and the general formula () (wherein, R 1 has the same meaning as in general formula ()), and the product is reduced with a metal hydride compound. General formula () (In the formula, R 1 has the same meaning as in the general formula ().) A method for producing cyclopentenes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6506081A JPS57179129A (en) | 1981-04-28 | 1981-04-28 | Cyclopentene derivative and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6506081A JPS57179129A (en) | 1981-04-28 | 1981-04-28 | Cyclopentene derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57179129A JPS57179129A (en) | 1982-11-04 |
| JPH0148252B2 true JPH0148252B2 (en) | 1989-10-18 |
Family
ID=13276023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6506081A Granted JPS57179129A (en) | 1981-04-28 | 1981-04-28 | Cyclopentene derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57179129A (en) |
-
1981
- 1981-04-28 JP JP6506081A patent/JPS57179129A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57179129A (en) | 1982-11-04 |
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