Dimethyl Sulfoxide → HCID 12272524, compound

Participants

Reaction Steps

To a dried flask under nitrogen was added dimethyl sulphoxide (100 ml) and tosmic (20.95 g, 107.3 mmol). The reaction mixture was cooled to 0° C. before potassium t-butoxide (33.35° g, 297.1 mmol) was added. After 5 min, methanol (3.7 ml) was added followed by 1-(2-pyridinyl)ethanone (10 g, 32.5 mmol) and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was poured in brine:hexane:ethyl acetate (50:25:25). The organic extracts were dried (Na2SO4) and concentrated in vacuo to yield a crude oil. The oil was purified by flash chromatography eluting with ethyl acetate:hexane (3:7) to give the title compound as a brown solid (8.26 g, 76%).

Provenance & Evidence