Hydrochloric Acid → 1,4-Anhydro-2,5-dideoxy-2-(methoxycarbonyl)-1-thiopent-3-ulose

Participants

Reaction Steps

To a solution of methyl 3-(2-ethoxy-1-methyl-2-oxo-ethyl)sulfanylpropanoate (2.2 g, 10 mmol) in methanol (15 mL) at 0° C. was added sodium methoxide (886 mg, 16.4 mmol). The reaction was warmed to rt and stirred for 3 h. The mixture was acidified with 1 N HCl to pH 2 and extracted with DCM. The organic phase was washed with water and brine, dried (Na2SO4), concentrated and purified by column chromatography, eluting with EtOAc in petroleum (3%-10%) to give methyl tetrahydro-5-methyl-4-oxothiophene-3-carboxylate as a colourless oil (0.85 g, 50% yield).

Provenance & Evidence