Dimethyl Sulfate → Tert-butyl 2-methoxyimino-3-phenyliminobutyrate

Participants

Reaction Steps

To a solution of tert-butyl 2-hydroxyimino-3-phenyliminobutyrate (1.0 g) in acetone (10 ml) was added potassium carbonate (0.63 g) and dimethyl sulfate (0.43 ml) under ice-cooling. The mixture was stirred at the same temperature for 30 minutes and stirred at ambient temperature for 4 hours. The resulting suspension was poured into ice-water and extracted with diisopropyl ether. The organic layer was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residual oil was subjected to column chromatography on silica gel give tert-butyl 2-methoxyimino-3-phenyliminobutyrate (0.68 g).

Provenance & Evidence