Sulfuric Acid → Methyl 4-oxooxolane-3-carboxylate

Participants

Reaction Steps

55% Sodium hydride (1.9 g) was suspended in tetrahydrofuran (30 ml), and a solution of methyl glycolate (3.6 g) in tetrahydrofuran (10 ml) was added dropwise over 10 minutes. After stirring at room temperature for 30 minutes, the solvent was evaporated to give a colorless solid. This was suspended in dimethyl sulfoxide (20 ml), and methyl acrylate (4.3 ml) was added under ice-cooling. The mixture was stirred at the same temperature for 15 minutes and then stirred at room temperature for 45 minutes. The reaction solution was poured into a 5% aqueous sulfuric acid solution (50 ml), followed by extraction with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane) to give the title compound (3.0 g) as a colorless solid.

Provenance & Evidence