KR800000624B1 - Process for preparing oxirane derivates - Google Patents

Process for preparing oxirane derivates Download PDF

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KR800000624B1
KR800000624B1 KR7600735A KR760000735A KR800000624B1 KR 800000624 B1 KR800000624 B1 KR 800000624B1 KR 7600735 A KR7600735 A KR 7600735A KR 760000735 A KR760000735 A KR 760000735A KR 800000624 B1 KR800000624 B1 KR 800000624B1
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trimethylsulfonium
oxirane
sulfate
mol
methyl
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KR7600735A
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Korean (ko)
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데루오 구쯔마
이찌가구 나가야마
도구지 오가자기
다다가쯔 시가모도
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오오다 쇼오죠오
오오다 세이야구 가브시기가이샤
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring

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Abstract

Title compds. (I, R1 = H, ring or chain hydrocarbon; ;R2 = chain or ring hydrocarbon, heterocyclic radical) were prepd. by reaction of trimethylsulfonium methylsulfate with aldehyde or ketone in the presence of bases. Thus, 7.99 g sodium methoxide was added to a mixt. of 17.62 g p-isobutylacetophenone and 28.24 g trimethylsulfonium methylsufate in 100 m1 acetonitrile, and stirred at room temp. for 10 min to give 15.99 g 2-(4'-isobutylpheny1)-2-methyloxirane.

Description

옥시란 유도체의 제조방법Method for preparing oxirane derivative

본 발명은 옥시란 유도체의 제조방법에 관한 것이다.The present invention relates to a method for preparing an oxirane derivative.

더욱, 상세하게 말하면, 본 발명은 일반식,More specifically, the present invention is a general formula,

Figure kpo00001
Figure kpo00001

(식중, R1은 수소원자이거나 또는 치환 혹은 비치환의 쇄상 혹은 환상의 탄화수소이고 R2는 치환 혹은 비치환의 쇄상 혹은 환상의 탄화수소기 또는 복소환식기이고 또 R1과 R2는 다같이 환을 형성할 수가 있다)로 표시되는 옥시란 유도체의 제조방법에 관한 것이다. 옥시란 유도체는 여러가지의 유용한 유기화학 물을 합성하기 위한 중간체 원료로서 극히 유용한 화합물이다. 종래에, 이들 옥시란 유도체의 제조방법의 하나로서 카르보닐 화합물에, 옥화트리메틸술포늄 또는 옥화트리메틸술 폭소늄을 반응시키는 방법이 알려져 있다(J,A,C,S, 87, 1353 (1965)).Wherein R 1 is a hydrogen atom or a substituted or unsubstituted chain or cyclic hydrocarbon, R 2 is a substituted or unsubstituted chain or cyclic hydrocarbon group or a heterocyclic group, and R 1 and R 2 together form a ring; A method for producing an oxirane derivative is shown. Oxirane derivatives are extremely useful compounds as intermediate raw materials for the synthesis of various useful organic chemicals. Conventionally, as one of the methods for producing these oxirane derivatives, a method of reacting a carbonyl compound with trimethylsulfonium iodide or trimethylsulfonium iodide is known (J, A, C, S, 87, 1353 (1965)). ).

그러나, 이들 옥화물은 그의 합성에 공업상난점이 있기 때문에 이들 옥화물을 사용하는 옥시란 유도체의 제조방법은 공업적으로는 대단히 불리한 점이 있었다.However, since these oxides have industrial difficulties in their synthesis, the method for producing oxirane derivatives using these oxides has been very disadvantageous industrially.

본 발명은 이들 불리한점을 극복한 신규한 공업적인 옥시란 유도체의 제조방법을 제공하는 것이다. 즉, 종래에, 옥화트리메틸술포늄의 합성에 있어서는 옥화메틸이 사용되나 이 옥화메틸은 비등점이 낮기때문에 취급상 난점이 있고 또 그것자체가 고가이므로 이러한 옥화메틸을 사용하지 않으면 제조할 수 없는 옥화트리메틸술포늄의 사용에 의한 옥시란 유도체의 제조방법은 공업적 제조방법으로서 불리하고 그점에 관하여 해결할 수 있는 과제로 되여 있었다.The present invention provides a novel method for preparing an industrial oxirane derivative that overcomes these disadvantages. That is, conventionally, methyl iodide is used in the synthesis of trimethyl sulfonium iodide. However, since methyl iodide has a low boiling point, it is difficult to handle and its price is expensive, so trimethyl iodide cannot be produced without using such methyl iodide. The method for producing an oxirane derivative by the use of sulfonium has been disadvantageous as an industrial production method and has been a problem that can be solved in that respect.

본 발명자들은 이러한 불리한점이 없는 상기한 옥시란 유도체의 제조방법을 탐구한 결과 카르보닐 화합물을 처리할때의 시약으로서 메틸황산트리메틸술포늄의 취급의 용이성, 경제성, 반응성에서 극히 유리한 시약인 것을 발견하였다. 본 발명은 이러한 견해에 기인하여 달성된 것이다.The present inventors have explored the above-described method for preparing an oxirane derivative without such disadvantages and found that it is an extremely advantageous reagent in the handling, economical efficiency and reactivity of trimethylsulfonium methyl sulfate as a reagent when treating a carbonyl compound. . The present invention has been accomplished based on this view.

본 발명에 의한 옥시란 유도체의 제조방법은 일반식Method for producing an oxirane derivative according to the present invention is a general formula

Figure kpo00002
Figure kpo00002

(식중 R1은 수소원자이거나 또는 치환 혹은 비치환의 쇄상 혹은 환상인 탄화수소기이고, R2는 치환 또는 비치환의 쇄상 또는 환상인 탄화수소기 또는 복소환식기인데 이들의 환상기는 복수의 환으로되는 축합환이라도 좋고 또 R1과 R2는 다같이 환을 형성할 수가 있다)로 표시되는 알데히드 혹은 케톤을 염기의 존재하에서 메틸황산트리메틸술포늄과 반응시키는 것을 특징으로 한다.(Wherein R 1 is a hydrogen atom or a substituted or unsubstituted chain or cyclic hydrocarbon group, R 2 is a substituted or unsubstituted chain or cyclic hydrocarbon group or a heterocyclic group, and these cyclic groups are condensed rings composed of a plurality of rings) Aldehyde or ketone represented by R 1 and R 2 may form a ring together with trimethylsulfonium methyl sulfate in the presence of a base.

본 발명의 방법을 더 상세하게 설명하면 일반식,In more detail the method of the present invention,

Figure kpo00003
Figure kpo00003

(식중 R1및 R2는 전술한 정의대로이다)로 표시되는 화합물을 적당한 유기용매에 용해하고 메틸황산트리메틸술포늄을 가한다. 적당한 유기용매로서는 아세트니트릴, 프로피오니트릴, 테트라히드로폴란, 디옥산, 디메틸술폭시드 등은 예시할 수 있다. 그다음 염기를 가하고 교반하여서 반응을 행할 수가 있다. 이 염기의 적당한 예로서는 NaH, CH3ONa, t-C4H9OK 등을 들수 있다.The compounds represented by the formula (wherein R 1 and R 2 are as defined above) are dissolved in a suitable organic solvent and methyl methylsulfonium sulfate is added. Examples of suitable organic solvents include acetonitrile, propionitrile, tetrahydropolan, dioxane, dimethyl sulfoxide and the like. The reaction can then be carried out by adding a base and stirring. Suitable examples of this base include NaH, CH 3 ONa, tC 4 H 9 OK, and the like.

적당한 처리온도는 예를들면 0°-80°C이다. 반응은 단시간에 용이하게 진행하는데 상기한 교반은 예를 들면 10분~수십분 정도라도 총분한 결과를 얻을 수가 있다.Suitable treatment temperatures are, for example, 0 ° -80 ° C. The reaction proceeds easily in a short time, but the above agitation can yield a total result even if it is about 10 minutes to several ten minutes.

본 발명의 방법에서 사용되는 메틸황산트리메틸술포늄은 유화디메틸과 황산디메틸을 유기용매 예를들면 메탄올, 에탄올, 테트라히드로폴란, 염화메틸렌, 아세트니트릴 등의 용매중에서 반응시키는 것에 의하여 정량적으로 얻어진다.The trimethylsulfonium methyl sulfate used in the method of the present invention is obtained quantitatively by reacting dimethyl emulsion and dimethyl sulfate in an organic solvent such as methanol, ethanol, tetrahydropolan, methylene chloride, acetonitrile and the like.

종래에 이 메틸황산트리메틸술포늄은 제초제로 이용되었고 용이하게 제조 또는 입수할 수 있는 물질이나, 본 발명자등은 이 물질을 옥시란 유도체의 합성한 시약으로서 이용하고 공업적으로 유리한 옥시란 유도체의 제조방법을 제공할 수 있었던 것이다.Conventionally, this methyl trimethylsulfonium has been used as a herbicide and can be easily produced or obtained, but the present inventors have used this substance as a synthetic reagent for oxirane derivatives, and produced industrially advantageous oxirane derivatives. It could provide a way.

트리메틸술포늄염을 사용하는 옥시란 유도체의 합성반응에서는 유화디메틸의 생성은 피할수 없는 것이어서, 본 발명의 방법에서도 그것의 생성은 볼수 있으나 유화디메틸은 불쾌한 냄새가 있고 이것의 생성이 종래 기술에서 극복할 과제의 하나로 되여 있었다.In the synthesis of oxirane derivatives using trimethylsulfonium salts, the production of dimethyl emulsion is unavoidable. Thus, even in the process of the present invention, the production of dimethyl emulsion is seen, but dimethyl emulsion has an unpleasant odor and its production is overcome in the prior art. It was one of the tasks.

본 발명자들은 이 과제에 대하여서도 다음과 같은 수단으로 해결하는 것에 성공하였다.The present inventors succeeded in solving this problem also with the following means.

즉, 그 수단이라는 것은 본 발명의 방법에서 반응할때에 사용하는 용매로서, 유화디메틸과 함께 유거할 수 있는 정도의 비등점을 가진 용매를 사용하고 반응이 종료할때에 유화디메틸과 이 용매를 함께 유거하고 그 증류물의 수용기에 황산디메틸을 미리 가하여 놓고 수용기중에서 메틸황산트리메틸술포늄을 생성시켜 이 메틸황산트리메틸술포늄을 다시 본 발명의 방법의 원료 카르보닐 화합물과 반응시키기 위해 사용하는 것으로 된다.That is, the means is a solvent used when reacting in the method of the present invention, using a solvent having a boiling point that can be distilled together with dimethyl emulsification, and when the reaction is complete After distillation, dimethyl sulfate is added to the receiver of the distillate in advance, methyl methyl sulfate sulfonium is produced in the receiver, and this methyl trisulfonium sulfate is used to react with the raw carbonyl compound of the method of the present invention again.

이하에 구체예를 들어 본 발명을 설명한다.An example is given to the following and this invention is demonstrated.

[실시예 1]Example 1

P-이소부틸아세트페논 17.62g(0.10몰), 메틸황산트리메틸술포늄28.24g(0.15몰)을 아세트니트릴 100ml에 용해한다.17.62 g (0.10 mole) of P-isobutylacetphenone and 28.24 g (0.15 mole) of methylmethylsulfonium sulfate are dissolved in 100 ml of acetonitrile.

실온, 교반하에 나트륨메톡시드 7.99g(0.148몰)을 가하고 10분간 교반한다. 그다음 용매 아세트니트릴 및 생성한 유화디메틸을 유거하고 유출액은 황산디메틸 25g(0.2몰)로 처리하여 메틸황산트리메틸술포늄을 20.98g(74.2%) 회수하였다. 잔사에 물 50ml를 가하여 벤젠 100ml로 2회 추출하고 포화식 염수로 세척하고, 무수황산나트륨으로 건조하고 벤젠을 유거한다음 감압증류하면 b.p.2.5 96-97℃로 유출하는 2-(4′-이소부틸페닐)-2-메틸옥시란 15.99g(수율 84.0%)의 무색한 액체로서 얻어진다.7.99 g (0.148 mol) of sodium methoxide is added at room temperature and with stirring, followed by stirring for 10 minutes. The solvent acetonitrile and the resulting dimethyl emulsified were then distilled off, and the effluent was treated with 25 g (0.2 mol) of dimethyl sulfate to recover 20.98 g (74.2%) of trimethylsulfonium methyl sulfate. 50 ml of water was added to the residue, extracted twice with 100 ml of benzene, washed with saturated brine, dried over anhydrous sodium sulfate, the benzene was distilled off, and distilled under reduced pressure to give 2- (4′-isobutyl) at bp2.5 96-97 ℃. Phenyl) -2-methyloxirane is obtained as a colorless liquid of 15.99 g (yield 84.0%).

NMR(CDCl3중)NMR in CDCl 3

δ 0.89(6HdJ = 7.5Hz(CH3)2CH-CH2-)δ 0.89 (6HdJ = 7.5 Hz (CH 3 ) 2 CH-CH 2- )

1.67(3H s. H3C

Figure kpo00004
1.67 (3 H s. H 3 C
Figure kpo00004

1.4-2.1(1Hm(CH2-CH-CH2-)1.4-2.1 (1Hm (CH 2 -CH-CH 2- )

2.43(2HdJ = 7.5Hz(CH3)2-CH-CH2-2.43 (2HdJ = 7.5 Hz (CH 3 ) 2 -CH-CH 2-

2.80 및 2.90(각 1HdJ = 6Hz

Figure kpo00005
2.80 and 2.90 (1 HdJ = 6 Hz each)
Figure kpo00005

6.95 및 7.15(각 2HdJ = 8Hz arom)6.95 and 7.15 (2HdJ = 8 Hz arom each)

MassMass

m/e 190(M+)m / e 190 (M + )

원소 분석치 C13H18O로서Elemental Analysis C 13 H 18 O

C% H%C% H%

계 산 치 82.06 9.54Calculated Value 82.06 9.54

실 험 치 82.00 9.51EXP 82.00 9.51

[실시예 2-9]Example 2-9

실시예 1과 같이하여, 아래 식에 나타내는 바와 같은 반응을 행하였다.In the same manner as in Example 1, the reaction was performed as shown in the following formula.

Figure kpo00006
Figure kpo00006

그 결과를 아래표에 표시한다. 표중, R1,R2는 생성 옥시란화합물의 식에 나타난 치환기를 표시한다.The results are shown in the table below. In the table, R 1 and R 2 represent a substituent shown in the formula of the resulting oxirane compound.

[표][table]

Figure kpo00007
Figure kpo00007

[실시예 10]Example 10

2-아세트나프톤 8.51g(0.05몰) 메틸황산트리메틸술포늄 14.12g(0.075몰)을 아세트니트릴 50ml에 용해하고, 실온, 교반하에 나트륨메톡시드 4.05g(0.075몰)을 가한다. 20분간 교반한후, 아세트니트릴 및 유화디메틸을 유거하고 유출액은 황산디메틸 12.6g(0.1몰)로 처리한다.8.51 g (0.05 mol) of 2-acetnaphtone 14.12 g (0.075 mol) methyltrimethylsulfonium sulfate is dissolved in 50 ml of acetonitrile, and 4.05 g (0.075 mol) of sodium methoxide is added under stirring at room temperature. After stirring for 20 minutes, acetonitrile and dimethyl emulsion are distilled off and the effluent is treated with 12.6 g (0.1 mol) of dimethyl sulfate.

잔사에 물 25ml를 가하여, 에테르 50ml로 2회 추출하여 포화식염수로 세척하고 무수황산나트륨으로 건조하여 에테르를 유거하고, 에탄올에서 재결정하면 융점 75-77°C의 2-메틸-2-(2-나프틸) 옥시란의 결정체로서 7.85g(수율 85.2%)를 얻어진다.To the residue was added 25 ml of water, extracted twice with 50 ml of ether, washed with brine, dried over anhydrous sodium sulfate, and the ether was distilled off. When recrystallized from ethanol, 2-methyl-2- (2-naph) with a melting point of 75-77 ° C 7.85 g (yield 85.2%) are obtained as crystals of butyl) oxirane.

NMR(CDCl3중)NMR in CDCl 3

δ 1.75(3H s. H3C

Figure kpo00008
)δ 1.75 (3H s. H 3 C
Figure kpo00008
)

2.78 및 2.97(각 1Hd J =6Hz

Figure kpo00009
)2.78 and 2.97 (1 Hd J = 6 Hz each)
Figure kpo00009
)

7.10~8.00(7H m. arom)7.10-8.00 (7H m. Arom)

MassMass

m/e 184(M+)m / e 184 (M + )

원소 분석치 C13H12O로서Elemental Analysis C 13 H 12 O

C% H%C% H%

계 산 치 84.75 6.57Calculated Value 84.75 6.57

실 험 치 84.71 6.52EXP 84.71 6.52

[실시예 11]Example 11

4-아세틸비페닐 9.81g(0.05몰), 메틸황산트리메틸술포늄 14.12g(0.075몰)을 아세트니트릴 50ml에 현탁시키고 실온, 교반하에 나트륨메톡시드 4.05g(0.075몰)을 가하여 20분간 교반한다.9.81 g (0.05 mol) of 4-acetylbiphenyl and 14.12 g (0.075 mol) of methyl sulfate trimethylsulfonium are suspended in 50 ml of acetonitrile, and 4.05 g (0.075 mol) of sodium methoxide is added thereto under stirring at room temperature and stirred for 20 minutes.

전기한 실시예와 같이 처리한후 N-헥산에서 재결정하면 융점 76-81°C의 2-( 4-비페니닐-2-메틸옥시란이 결정체로서 9.09g(수율 86.5%)가 얻어진다.After the treatment as described in the above Example, the crystallization of N-hexane to give a 9.09g (yield 86.5%) of 2- (4-bipheninyl-2-methyloxirane as crystals at a melting point of 76-81 ° C.

NMR(CDCl3중)NMR in CDCl 3

δ 1.70(3H, s. H3C

Figure kpo00010
δ 1.70 (3H, s. H 3 C
Figure kpo00010

2.72 및 2.91(각 1 Hd. J =6Hz)2.72 and 2.91 (1 Hd. J = 6 Hz each)

7.45(9H m. arom)7.45 (9 H m. Arom)

MassMass

m/e 210(M+)m / e 210 (M + )

원소 분석치 C15H14O로서Elemental Analysis C 15 H 14 O

C% H%C% H%

계 산 치 85.68 6.71Calculated Value 85.68 6.71

실 험 치 85.13 7.01EXP 85.13 7.01

[실시예 12]Example 12

4-아세틸피리딘 6.05g(0.05몰), 메틸황산트리메틸술포늄 14.12g(0.075몰)을 아세트니트릴 50ml에 용해하고, 실온, 교반하에 나트륨 메톡시드 4.05g(0.075몰)을 가한다.6.05 g (0.05 mol) of 4-acetylpyridine and 14.12 g (0.075 mol) of methyl sulfate trimethylsulfonium are dissolved in 50 ml of acetonitrile, and 4.05 g (0.075 mol) of sodium methoxide is added at room temperature and with stirring.

실시예 1과 같이 처리하고 감압증류하면 b.p 9-10 86-88°C의 2-메틸-2-(4-피리딘) 옥시란이 황색액체로서 4.05g(수율 60.0%)이 얻어졌다.After treating as in Example 1 and distillation under reduced pressure, 4.05 g (yield 60.0%) of 2-methyl-2- (4-pyridine) oxirane of b.p 9-10 86-88 ° C was obtained as a yellow liquid.

NMR(CDCl3중)NMR in CDCl 3

δ 1.68(3H s.H3C

Figure kpo00011
)δ 1.68 (3H sH 3 C
Figure kpo00011
)

2.72 및 2.95(각 1Hd. J =5.5Hz)2.72 and 2.95 (1 Hd. J = 5.5 Hz each)

7.24 및 8.55(각 2Hd. J =5 1.5Hz)7.24 and 8.55 (2Hd. J = 5 1.5 Hz each)

MassMass

m/e 135(M+)m / e 135 (M + )

원소 분석치 C8H9NO로서Elemental Analysis C 8 H 9 NO

C% H% N%C% H% N%

계 산 치 71.09 6.71 10.36Calculated Value 71.09 6.71 10.36

실 험 치 71.58 7.41 9.51EXP 71.58 7.41 9.51

[실시예 13]Example 13

2-아세틸벤조폴란 8.00g(0.05몰)과 케틸황산트리메틸술포늄 14.12g(0.075몰)을 아세트니트릴 50ml에 용해하고 실온 교반하여 나트륨 메톡시드 4.05g(0.075몰)을 가하고 20분간 교반한다.8.00 g (0.05 mole) of 2-acetylbenzopolan and 14.12 g (0.075 mole) of trimethylsulfonium ketyl sulfate are dissolved in 50 ml of acetonitrile, and stirred at room temperature, 4.05 g (0.075 mole) of sodium methoxide is added and stirred for 20 minutes.

전기한 실시예와 같이 처리하고 아세톤에서 재결정하면 융점 60-61°C의 2-(2-벤조푸라닐)-2-메틸옥시란이 결정체로서 7.61g(수율 87.5%)이 얻어진다.When treated in the same manner as described above and recrystallized in acetone, 7.61 g (yield 87.5%) of 2- (2-benzofuranyl) -2-methyloxirane at a melting point of 60-61 ° C is obtained as crystals.

NMR(CDCl3중)NMR in CDCl 3

δ 1.75(3H s.H3C

Figure kpo00012
)δ 1.75 (3H sH 3 C
Figure kpo00012
)

2.95 및 3.47(각 1Hd J =5.5Hz

Figure kpo00013
)2.95 and 3.47 (1 Hd J = 5.5 Hz each)
Figure kpo00013
)

6.67(1H s.

Figure kpo00014
)6.67 (1 H s.
Figure kpo00014
)

7.0-7.5(4H m. arom)7.0-7.5 (4H m. Arom)

MassMass

m/e 174(M+)m / e 174 (M + )

원소 분석치 C11H11O2로서Elemental Analysis C 11 H 11 O 2 As

C% H%C% H%

계 산 치 75.84 5.79Calculated Value 75.84 5.79

실 험 치 75.80 5.84EXP 75.80 5.84

[실시예 14]Example 14

2-아세틸페노티아딘 12.07g(0.05몰) 메틸황산트리메틸술포늄 14.12g(0.075몰)을 아세트니트릴 50ml에 용해하고, 실온, 교반하에 나트륨메톡시드 4.05g(0.05몰)을 가하고 60분간 교반한다.12.07 g (0.05 mol) of 2-acetylphenothiadine 14.12 g (0.075 mol) of methyl sulfate trimethylsulfonium is dissolved in 50 ml of acetonitrile, 4.05 g (0.05 mol) of sodium methoxide is added to the mixture at room temperature and stirred, followed by stirring for 60 minutes. .

전기한 실시예와 동양으로 처리하고 이소프로필에테르에서 재결정하면 융점 105-111℃의 2-메틸-2-(2-페노티아디닐) 올시란이 결정체로서 7.0g(수율 54.7%)가 얻어진다.When treated in the same manner as described above and recrystallized from isopropyl ether, 2-methyl-2- (2-phenothiadinyl) osilane having a melting point of 105-111 DEG C is obtained as crystals, and 7.0 g (yield 54.7%) is obtained. .

NMH(CDCl3중)NMH (in CDCl 3 )

δ 1.60(3H s.H3C

Figure kpo00015
)δ 1.60 (3H sH 3 C
Figure kpo00015
)

2.68-2.87(1H d. J =5.5Hz)2.68-2.87 (1H d. J = 5.5 Hz)

6.06(1H s.

Figure kpo00016
)6.06 (1 H s.
Figure kpo00016
)

6,52(3H m. arom)6,52 (3H m. Arom)

6.81(3H m. arom)6.81 (3 H m. Arom)

MassMass

m/e 255(M+)m / e 255 (M + )

원소 분석치 C15H13NOS로서Elemental Analysis C 15 H 13 As NOS

C% H% H%C% H% H%

계 산 치 70.56 5.13 5.49Calculated Value 70.56 5.13 5.49

실 험 치 70.91 4.83 5.95EXP 70.91 4.83 5.95

Claims (1)

다음 일반식Following formula
Figure kpo00017
Figure kpo00017
 로 표시되는 알데히드 혹은 케톤을 염기의 존재하에 메틸황산트리메틸술포늄과 반응시키는 것을 특징으로 하는 다음 일반식,The following general formula is characterized in that the aldehyde or ketone represented by the reaction with trimethylsulfonium methyl sulfate in the presence of a base,
Figure kpo00018
Figure kpo00018
 로 표시되는 옥시란 유도체의 제조방법. (식중 R1은 수소원자이거나 치환 또는 비치환의 쇄상 혹은 환상 탄화수소기이고 R2는 치환 흑은 비치환의 쇄상 또는 환상의 탄화수소기 또는 복소 환식기이고, 또 R1과 R2는 다같이 환을 형성할 수가 있다.)Method for producing an oxirane derivative represented by. (Wherein R 1 is a hydrogen atom or a substituted or unsubstituted chain or cyclic hydrocarbon group, R 2 is a substituted black unsubstituted chain or cyclic hydrocarbon group or a heterocyclic group, and R 1 and R 2 together form a ring) I can do it.)
KR7600735A 1976-03-25 1976-03-25 Process for preparing oxirane derivates KR800000624B1 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106518812A (en) * 2016-10-25 2017-03-22 湖南大学 Preparation method of medetomidine and intermediate thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106518812A (en) * 2016-10-25 2017-03-22 湖南大学 Preparation method of medetomidine and intermediate thereof

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