Hydrochloric Acid → Methyl 3-(i-propylsulfonyl)-2-oxopropanoate

Participants

Reaction Steps

To a mixture of i-propylmethylsulfone (5.17 g, 42.3 mmol) and THF (20 mL) was added 28% sodium methoxide methanol solution (8.58 g, 44.5 mmol) at room temperature, and then methyl oxalate (5.0 g, 42.3 mmol) was gradually added to the mixture at room temperature. The resulting mixture was stirred at room temperature overnight. To the reaction mixture was added ice-water (200 mL), and the pH of the resulting mixture was adjusted pH3 or less than pH3 with 2 mol/L hydrochloric acid. The mixture was extracted with ethyl acetate (200 mL). The extract was washed with brine (200 mL), dried over anhydrous sodium sulphate, and concentrated in vacuo. The resulting residue was purified on a silica gel column chromatography (ethyl acetate/n-hexane) to give methyl 3-(i-propylsulfonyl)-2-oxopropanoate (2.7 g, yield: 28%) as colorless oil.

Provenance & Evidence