반응 #8216

반응 방정식

bromoacetonitrile

indole

NaH

→

indol-1-yl-acetonitrile

수율 27.1%

용매

ethyl acetate

dimethylformamide

반응 조건

후처리

1. 1
   세척washed with H2O (3×200 ml)
2. 2
   건조The organic layer is dried over Na2SO4
3. 3
   농축concentrated in vacuo
4. 4
   기타The crude residue is purified by flash chromatography (SiO2

실험 절차

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%).

출처