Reacción #8216

Ecuación de reacción

bromoacetonitrile

indole

NaH

→

indol-1-yl-acetonitrile

Rendimiento 27.1%

Disolventes

ethyl acetate

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with H2O (3×200 ml)
2. 2
   SecadoThe organic layer is dried over Na2SO4
3. 3
   Concentraciónconcentrated in vacuo
4. 4
   OtroThe crude residue is purified by flash chromatography (SiO2

Procedimiento

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%).

Fuente