Acetone → 2-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide

Participants

Reaction Steps

A mixture of 2-(2-hydroxymethylphenyl)-2-hydroxyimino-N-methylacetamide (521 mg, E/Z≠93/7), potassium carbonate (415 mg), 95% dimethyl sulfate (365 mg) and acetone (5.0 ml) was stirred at room temperature for 6 hours. A few pieces of ice were added, and the mixture was stirred for 30 minutes. Water (about 50 ml) was added, and the mixture was extracted with ethyl acetate three times. The combined ethyl acetate layer was washed with saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure gave the crude product (E/Z≠9 97/3). The crude product was crystallized from ethyl acetate-hexane to obtain the title compound as crystals (389 mg) (E/Z=97/3, yield: 70.0%).

Provenance & Evidence