反应详情

A solution of 2-hydroxyimino-2-phenylacetonitrile (2.2 g.) and dimethylaniline (1.80 g.) in a mixture of benzene (25 ml.) and dioxane (3 ml.) was dropwise added to a solution of trichloromethyl chloroformate (phosgene dimer) (1.5 g.) in benzene (20 ml.) under ice-cooling. The mixture was stirred for 3 hours at the same temperature and allowed to stand overnight. To the resultant mixture containing 2-chlorocarbonyloxyimino-2-phenylacetonitrile was dropwise added a solution of 1-cyclopropylethanol (1.4 g.) and pyridine (1.2 ml.) in benzene (10 ml.) under ice-cooling. The mixture was stirred for 2 hours at the same temperature, for 4 hours at room temperature and allowed to stand overnight. The reaction mixture was in turn washed with 1N hydrochloric acid, water, a sodium bicarbonate aqueous solution and water, and dried over magnesium sulfate. The solvent was distilled off and to the oily residue was added a small amount of methanol. The mixture was allowed to stand in a refrigerator, and the precipitated crystals were collected by filtration and recrystallized from methanol to give 2-(1-cyclopropylethoxycarbonyloxyimino)-2-phenylacetonitrile (0.7 g.), mp 65° to 67° C.

1. temperaturecooling
2. waitto stand overnight
3. temperaturecooling
4. stirringThe mixture was stirred for 2 hours at the same temperature, for 4 hours at room temperature
5. waitto stand overnight
6. washwashed with 1N hydrochloric acid, water
7. dry with materiala sodium bicarbonate aqueous solution and water, and dried over magnesium sulfate
8. distillationThe solvent was distilled off and to the oily residue
9. additionwas added a small amount of methanol
10. filtrationthe precipitated crystals were collected by filtration
11. customrecrystallized from methanol