Sodium hydride → HCID 57000686, compound

Participants

Reaction Steps

0.68 g of 55% sodium hydride was mixed with 10 ml of dimethylformamide. A solution of 2.50g of 4-(4'-cyanophenyl)phenol in 5 ml of dimethylformamide was added dropwise thereto under ice-cooling. Then the obtained mixture was stirred at room temperature for one hour. A solution of 3.7 g of monotosylate of (R,R)-2,4-pentanediol in 5 ml of dimethylformamide was added dropwise thereto and the obtained mixture was stirred at 80° C. for two hours. After cooling, the reaction mixture was poured into 100 ml of ice-water and extracted with diethyl ether. After washing with water, drying and desolvating, the obtained residue was purified by silica gel column chromatography with the use of a mixture of n-hexane and ethyl acetate (3:2) as a developing solvent. Thus 1.8 g of (R,S)-4-[4'-(3"-hydroxy-1"-methylbutoxy)phenyl]benzonitrile was obtained.

Provenance & Evidence