反应 #8216

反应方程式

bromoacetonitrile

indole

NaH

→

indol-1-yl-acetonitrile

收率 27.1%

溶剂

ethyl acetate

dimethylformamide

反应条件

后处理

1. 1
   洗涤washed with H2O (3×200 ml)
2. 2
   干燥The organic layer is dried over Na2SO4
3. 3
   浓缩concentrated in vacuo
4. 4
   其他The crude residue is purified by flash chromatography (SiO2

实验过程

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%).

来源