Reacción #8215

Ecuación de reacción

bromoacetonitrile

4-hydroxyindole

NaH

→

(1H-indol-4-yloxy)acetonitrile

Rendimiento 97.0%

Disolventes

ethyl acetate

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed 3 times with H2O
2. 2
   SecadoThe organic layer is dried over Na2SO4
3. 3
   Concentraciónconcentrated in vacuo
4. 4
   OtroThe crude residue is purified by normal phase HPLC (SiO2; 5% step gradient of 0 to 20% ethyl acetate in hexanes)

Procedimiento

A 0° C. solution of 4-hydroxyindole (20 g, 150 mmol) in 500 ml of dimethylformamide is treated with NaH (60% dispersion in mineral oil; 6.6 g, 165 mmol). After 30 minutes, bromoacetonitrile (11.5 ml, 165 mmol) is added, and the resulting mixture is allowed to slowly warm to ambient temperature and stir for 3 days. The reaction mixture is diluted with ethyl acetate and washed 3 times with H2O. The organic layer is dried over Na2SO4 and concentrated in vacuo. The crude residue is purified by normal phase HPLC (SiO2; 5% step gradient of 0 to 20% ethyl acetate in hexanes) to give 25 g of (1H-indol-4-yloxy)acetonitrile (97%).

Fuente