Sodium hydride → 3-Cyclopropyl-3-oxo-2-[(2'-nitrobiphen-4-yl)methyl]propanenitrile

HRID 257255

反応式

HRID 257255 の反応式
[CH:1]1([C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N+:25]([O-:27])=[O:26])=[CH:15][CH:14]=1>CS(C)=O.[Cl-].[Na+].O>[CH:1]1([C:4](=[O:8])[CH:5]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N+:25]([O-:27])=[O:26])=[CH:17][CH:18]=2)[C:6]#[N:7])[CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 98127633-Cyclopropyl-3-oxopropanenitrileHCID 117790721,1'-Biphenyl, 4'-(bromomethyl)-2-nitro-

生成物 1

HCID 1317181973-Cyclopropyl-3-oxo-2-[(2'-nitrobiphen-4-yl)methyl]propanenitrile収率 34%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution of 2.61 g (24.0 mmol) 3-cyclopropyl-3-oxopropanenitrile in 150 mL DMSO was added 1.01 g (25.2 mmol) 60% NaH in oil. After 1 hour, 3.50 g (12.0 mmol) 4'-bromomethyl-2-nitrobiphenyl was added all at once to the solution. After 3 hours, the solution was poured into brine and extracted 3 times with ether. The combined organic material was dried over MgSO4, stripped of solvent in vacuo, and was chromatographed on silica gel under medium pressure using 3/40/57 EtOAc/CH2Cl2/hexanes to give 1.29 g (34% yield) of the title compound as a yellow glass. Rf 0.13 in 3/40/57 EtOAc/CH2Cl2/hexanes, visualized by UV and ammonium molybdate/ceric sulfate stain; Rf of the dialkylated material is 0.19 in the same solvent mixture.

後処理

  1. waitAfter 3 hours
  2. extractionextracted 3 times with ether
  3. dry with materialThe combined organic material was dried over MgSO4
  4. customwas chromatographed on silica gel under medium pressure

出典と根拠

ORDレコード
ord-50371f6999eb4c8eacd07d7b1e8acde9
出典データセット
uspto-grants-1993_11
特許番号
US05260285

関連ノート

読み込み中…