تفاعل #8216

معادلة التفاعل

bromoacetonitrile

indole

NaH

→

indol-1-yl-acetonitrile

المردود 27.1%

المذيبات

ethyl acetate

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with H2O (3×200 ml)
2. 2
   تجفيفThe organic layer is dried over Na2SO4
3. 3
   تركيزconcentrated in vacuo
4. 4
   أخرىThe crude residue is purified by flash chromatography (SiO2

الإجراء التجريبي

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%).

المصدر