反応 #8216

反応方程式

bromoacetonitrile

indole

NaH

→

indol-1-yl-acetonitrile

収率 27.1%

溶媒

ethyl acetate

dimethylformamide

反応条件

後処理

1. 1
   洗浄washed with H2O (3×200 ml)
2. 2
   乾燥The organic layer is dried over Na2SO4
3. 3
   濃縮concentrated in vacuo
4. 4
   その他The crude residue is purified by flash chromatography (SiO2

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%).

出典