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

HRID 610848ノート

反応式

HRID 610848 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2b0d60a93a304d6594dc6d994d7e9ec7
出典データセット
uspto-grants-1999_12
特許番号
US05998673

反応ノート

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