Water → HCID 86738077, 화합물

HRID 622723노트

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HRID 622723 반응식
[Cl:1]/[C:2](/[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[CH:3]\[C@H:4]1[C@H:6]([C:7](Cl)=[O:8])[C:5]1([CH3:11])[CH3:10].[C-:19]#[N:20].[Na+].O.[O:23]([C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][C:37]=1[F:38])[CH:33]=[O:34])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1CCCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:19]([CH:33]([O:34][C:7]([C@H:6]1[C@H:4](/[CH:3]=[C:2](\[Cl:1])/[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:5]1([CH3:11])[CH3:10])=[O:8])[C:32]1[CH:35]=[CH:36][C:37]([F:38])=[C:30]([O:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:31]=1)#[N:20]

참가 물질

8

반응물 4

HCID 962WaterHCID 8929Sodium CyanideHCID 1100684-Fluoro-3-phenoxybenzaldehydeHCID 44152741rel-(1R,3R)-3-[(1Z)-2-Chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropanecarbonyl chloride

생성물 1

HCID 86738077HCID 86738077, 화합물수율 77%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매HCID 8078Cyclohexane용매2회

실험 절차

3.4 g (0.0112 mole) of (+)-trans-Z-3-(2-chloro-2-(4-chloro-phenyl)-vinyl)-2,2-dimethyl-1-cyclopropanecarboxylic acid chloride, dissolved in 10 ml of cyclohexane, were added dropwise to a mixture of 50 ml of cyclohexane, 0.87 g of sodium cyanide, 1.3 ml of water, 2.42 g (0.0112 mole) of 3-phenoxy-4-fluorobenzaldehyde and 0.2 g of tetrabutylammonium bromide at 20°-25° C., whilst stirring, and the mixture was then stirred at 20°-25° C. for 4 hours. 100 ml of toluene were then added to the reaction mixture and the mixture was extracted twice by shaking with 60 ml of water each time. The organic phase was separated off and dried over magnesium sulphate and the solvent was distilled off under a waterpump vacuum. Last residues of solvent were removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg. 4.4 g (77% of theory) of (+)-trans-Z-3-(2-chloro-2-(4-chloro-phenyl)vinyl)-2,2-dimethyl-cyclopropane-carboxylic acid (±)-α-cyano-3-phenoxy-4-fluoro-benzyl ester were obtained as a viscous oil with an optical rotation [α]D of +58.2° (C=100 mg in 10 ml of CHCl3).

후처리

  1. stirringthe mixture was then stirred at 20°-25° C. for 4 hours
  2. extractionthe mixture was extracted twice
  3. stirringby shaking with 60 ml of water each time
  4. customThe organic phase was separated off
  5. dry with materialdried over magnesium sulphate
  6. distillationthe solvent was distilled off under a waterpump vacuum
  7. customLast residues of solvent were removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg

출처 및 근거

ORD 기록
ord-a7620ee028bc454fb53328517de23e9e
출처 데이터셋
uspto-grants-1988_09
특허 번호
US04772629

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