N,N-Dimethylaniline → 2-Tert-butoxycarbonyloxyimino-2-(1-naphthyl)acetonitrile

Participants

Reaction Steps

A solution of 2-hydroxyimino-2-(1-naphthyl)acetonitrile (7.0 g.) and dimethylaniline (12.0 g.) in toluene (100 ml.) was dropwise added under ice-cooling to a solution of trichloromethyl chloroformate (phosgene dimer) (3.56 g.) in benzene (30 ml.). The mixture was stirred for 3 hours at the same temperature and allowed to stand overnight. To the resultant mixture containing 2-chlorocarbonyloxyimino-2-(1-naphthyl)acetonitrile was dropwise added a solution of tert-butyl alcohol (11.1 g.) and pyridine (12 ml.) in toluene (20 ml.) under ice-cooling, and the mixture was stirred for 6 hours at the same temperature and allowed to stand overnight. The reaction mixture was in turn washed with water, 1N hydrochloric acid, water, a sodium bicarbonate aqueous solution and water, and dried over magnesium sulfate. The solution was concentrated under reduced pressure and to the residue were added n-hexane and methanol. The mixture was allowed to stand in a refrigerator, and the precipitated crystals were collected by filtration and recrystallized twice from methanol to give 2-tert-butoxycarbonyloxyimino-2-(1-naphthyl)acetonitrile (3.3 g.), mp 90° to 92° C.

Provenance & Evidence