Hydrochloric Acid → HCID 57977387, compound

Participants

Reaction Conditions

Reaction Steps

Under argon, 14.7 g of sodium hydride (60% in mineral oil) were added to 311 ml (332 g, 3.685 mol) of dimethyl carbonate, and the mixture was heated to 80° C. A solution of 41 g (0.217 mol) of methyl (3-methylthiophen-2-yl)acetate in 50 ml of toluene was slowly added dropwise at this temperature, and the mixture was stirred at reflux overnight. For work-up, the mixture was diluted with about 200 ml of methanol, poured into ice-water and acidified with dilute hydrochloric acid. Extraction with dichloromethane, drying of the organic phase over sodium sulphate, filtration and removal of the solvent gave 43.6 g of dimethyl 2-(3-methylthiophen-2-yl)malonate. Yield: 88%. 1H-NMR (DMSO): δ=7.42 (d, 1H), 6.89 (d, 1H), 5.27 (s, 1H), 3.69 (s, 6H), 2.15 (s, 3H).

Provenance & Evidence