Water → 1-(3,4-Dimethoxyphenoxy)-3-nitropropan-2-one

Participants

Reaction Steps

To a suspension of potassium tert-butoxide (3.38 g) in DMSO (60 ml), a solution of nitromethane (0.836 g) in DMSO (5 ml) was added at 10° C. and the mixture was stirred at the same temperature for 30 minutes. A DMSO (65 ml) suspension of the compound (4.30 g) obtained in Example 19-(1) was added dropwise at 10° C. and the mixture was stirred at the same temperature for an hour, then at room temperature for 3 hours. The reaction mixture was poured into water (250 ml), rendered acidic with 10% aqueous acetic acid, and subjected to extraction with AcOEt. The organic layer was washed with water, dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by silica gel chromatography (AcOEt/hexane) and then recrystallized (AcOEt/hexane) to give the titled compound (0.808 g, pale yellow solid.)

Provenance & Evidence