Dimethyl Sulfoxide → HCID 20770558, compound

Participants

Reaction Steps

Methyl phenylsulfonylacetate (5 g, 23.3 mmol) was mixed with carbon disulfide (1.77 g, 23.3 mmol) in anhydrous DMSO (100 ml) at room temperature. Sodium hydride (60% in mineral oil, 1.2 g, 48.9 mmol) was added portionwise. After stirring at room temperature for 1 hour, iodomethane (6.9 g, 48.9 mmol) was added neat and the reaction mixture was stirred overnight. The reaction mixture was quenched by the addition of water, and the resulting mixture extracted with dichloromethane. The organic layer was purified via flash chromatography and concentrated in vacuo to provide crude 2-benzenesulfonyl-3,3-bis-methylsulfanyl-acrylic acid methyl ester, which was further purified by recrystallization from methanol to yield 3.7 grams of white solid. 1H NMR (500 MHz, CDCl3): δ 8.1 (d, 2H), 7.6 (t, 1H), 7.5 (t, 2H), 3.9 (s, 3H), 2.4 (s, 3H), 2.2 (s, 3H).

Provenance & Evidence