Dimethyl Sulfide → HCID 69731969, compound

Participants

Reaction Conditions

Reaction Steps

Compound 1b (2.0 g, 4.5 mmol) was dissolved in acetonitrile. Dimethylsulfide (6.6 mL) and acetic acid (2 mL) were added and the resulting mixture cooled to 0-5° C. (ice bath) under nitrogen. Benzoyl peroxide (6.36 g, 26 mmol) was added in several portions over 5 hours, then stirred for an additional 10 minutes, and then the reaction mixture was poured into a mixture of ethyl acetate and saturated aq. sodium bicarbonate (100 mL each). The organic phase was separated, rinsed with water, brine (×2), and concentrated in vacuo to give a gum. This gum upon addition of 50 mL of diethyl ether afforded 1.56 g (70%) of an off a white crystalline solid. m.p.=159-160° C. Spectral data were consistent with the title compound.

Provenance & Evidence