Dimethyl Sulfoxide → HCID 86701117, compound

Participants

Reaction Conditions

Reaction Steps

A solution of DMSO (52 g, 672 mmol) in dichloromethane (500 mL) was treated with oxalyl dichloride (64 g, 505 mmol) at −78° C. for 1 hour, then a solution of 117 (36 g, 84 mmol) in dichloromethane (150 mL) was added. The resulted solution was stirred for 4 hours at −20° C. followed by the addition of triethylamine (85 g, 841 mmol) at −78° C. After stirring at −20° C. for additional 1 hour, the reaction was quenched with water (600 mL), extracted with dichloromethane (2×300 mL). The organic layers combined, washed with brine (2×200 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a residue, which was purified by silica gel column, eluted with 3% 20% ethyl acetate in petroleum ether to afford 118 (26 g, 73%) as a yellow syrup; [M+H]+ 427.0; 1H NMR (300 MHz, CDCl3) δ 6.02 (d, J=6.3 Hz, 1H), 5.82-5.99 (m, 2H), 5.17-5.35 (m, 4H), 4.20-4.29 (m, 1H), 4.03-4.29 (m, 5H), 3.71-3.77 (m, 2H), 3.25 (s, 3H), 2.14 (s, 3H), 1.52 (s, 9H).

Provenance & Evidence