Dimethyl Sulfoxide → HCID 70391478, compound

Participants

Reaction Steps

To a solution of 4.65 g (29.0 mmol) of 4-carbomethoxytetrahydro-3-thiophenone in 20 ml of dry DMSO cooled in a cold-water bath at 12° C. under argon was added 1.73 g (32.0 mmol) of sodium methoxide. The mixture was stirred 30 minutes and a solution of 4.97 g (35.0 mmol) of methyl iodide in 1 ml of dry DMSO was added dropwise. The mixture was stirred overnight at room temperature, than diluted with water (60 ml) and extracted with methylene chloride (3×75 ml). The extract was washed with water (50 ml) and brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 5.4 g of an oil. The oil was flash chromatographed on silica gel eluting with 3:1 hexane:ether to give 1.49 g (30%) of the product as an oil; NMR (deuteriochloroform): δ 3.76 (S, 3H), 3.70 (m, 1H), 3.50 (dd, 1H), 3.30 (dd, 1H), 2.83 (d, 1H), 1.46 (S, 3H).

Provenance & Evidence