Water → Benzeneacetamide

Participants

Reaction Steps

2-(Hydroxymethyl)-α-(methoxyimino)-N-methyl-benzeneacetamide (0.46 g, 2.07 mmol) was dissolved with stirring in anhydrous dimethyl sulphoxide (20 mL) and 60% sodium hydride (0.10 g, 2.5 mmol) added. The reaction mixture was stirred at room temperature for 20 minutes and a solution of 2-(2,2-dimethylethyl)-2-(5-methyl-6-methylsulphonyl-3-pyridinyl)-1,3-dioxolane (0.62 g, 2.07 mmol) in anhydrous dimethyl sulphoxide (5 mL) added. The reaction mixture was heated to 45° C. and stirred overnight. It was then cooled to room temperature and poured into water. This was extracted with ethyl acetate (2×40 mL), the organic extracts combined and washed with water and brine, and dried (Na2SO4). Evaporation of the solvent under reduced pressure and purification of the residue by chromatography over silica (10-50% ethyl acetate:pentane) gave the desired product (0.37 g, 40%) as a clear gum.

Provenance & Evidence