反应详情

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.

1. waitto stand overnight
2. temperaturecooling
3. stirringthe mixture was stirred for 6 hours at the same temperature
4. waitto stand overnight
5. washwashed with water, 1N hydrochloric acid, water
6. dry with materiala sodium bicarbonate aqueous solution and water, and dried over magnesium sulfate
7. concentrationThe solution was concentrated under reduced pressure and to the residue
8. additionwere added n-hexane and methanol
9. filtrationthe precipitated crystals were collected by filtration
10. customrecrystallized twice from methanol