Indole → 1H-Indole-1-acetonitrile

HRID 1072614ノート

反応式

HRID 1072614 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].Br[CH2:13][C:14]#[N:15]>CN(C)C=O.C(OCC)(=O)C>[N:1]1([CH2:13][C:14]#[N:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

参加物

6

反応物 3

HCID 798IndoleHCID 11534BromoacetonitrileHCID 24758Sodium hydride

生成物 1

HCID 122309041H-Indole-1-acetonitrile収率 27.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A 0° C. solution of indole (7 g, 59.8 mmol) in 200 ml of dimethylformamide is treated with NaH (60% dispersion in mineral oil; 3.1 g, 77.7 mmol). After 20 minutes, bromoacetonitrile (4.2 ml, 59.8 mmol) is added, and the resulting mixture is allowed to slowly warm to ambient temperature and stir overnight. The reaction mixture is diluted with ethyl acetate (500 ml) and washed with H2O (3×200 ml). The organic layer is dried over Na2SO4 and concentrated in vacuo. The crude residue is purified by flash chromatography (SiO2; 5% then 20% ethyl acetate in hexanes) to give 2.53 g of indol-1-yl-acetonitrile (27%).

後処理

  1. washwashed with H2O (3×200 ml)
  2. dry with materialThe organic layer is dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude residue is purified by flash chromatography (SiO2

出典と根拠

ORDレコード
ord-1bd3b4102d7041c39f77b46820cdcbb8
出典データセット
uspto-grants-2005_06
特許番号
US06911463B2

反応ノート

読み込み中…