Cesium fluoride → 4-(p-Chlorophenyl)-3-fluoro-4-methyl-2-pentenenitrile

HRID 1977707노트

반응식

HRID 1977707 반응식
[F-:1].[Cs+].F.[K].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:18])([CH3:17])[C:13]#[C:14][C:15]#[N:16])=[CH:8][CH:7]=1.C(OCC)(=O)C.CCCCCC>CN(C)C=O.O>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([CH3:18])([CH3:17])[C:13]([F:1])=[CH:14][C:15]#[N:16])=[CH:10][CH:11]=1

참가 물질

7

반응물 4

HCID 25953Cesium fluorideHCID 21226206Ethyl acetate hexaneHCID 219955344-(p-Chlorophenyl)-4-methyl-2-pentynenitrileHCID 53443437Potassium fluoride, 99%, spray-dried

생성물 1

HCID 542690284-(p-Chlorophenyl)-3-fluoro-4-methyl-2-pentenenitrile수율 76.8%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6228Dimethylformamide용매2회

실험 절차

A mixture of cesium fluoride (41.38 g, 0.272 mol), potassium hydrogen fluoride (10.64 g, 0.136 mol) and water (13.07 g, 0.726 mol) in N,N-dimethylformamide is stirred for 10 minutes, treated with a solution of 4-(p-chlorophenyl)-4-methyl-2-pentynenitrile (18.5 g, 0.091 mol) in N,N-dimethylformamide, stirred at 80-85° C. for 4 hours, stirred at room temperature overnight and diluted with water. The aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. Column chromatography of the residue using silica gel and a 1:9 ethyl acetate/hexane solution gives the title product as an oil (15.6 g, 76.8% yield).

후처리

  1. stirringstirred at 80-85° C. for 4 hours
  2. stirringstirred at room temperature overnight
  3. extractionThe aqueous mixture is extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a residue

출처 및 근거

ORD 기록
ord-70d2c4993ec342b99830239e217e7f0e
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06235754B1

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