Dimethyl Sulfoxide → HCID 86701120, compound

Participants

Reaction Conditions

Reaction Steps

A solution of DMSO (40 g, 0.52 mol) in anhydrous dichloromethane (1.5 L) was treated with oxallyl dichloride (49 g, 0.39 mol) at −78° C. for 1 hour, followed by addition of 123 (30 g, 65 mmol). The resulting solution was stirred for 4 hours at −30° C. and then cooled down to −78° C. again at which time triethylamine (86 g, 0.85 mol) was added. After 1 hour at −50° C., the reaction mixture was quenched by H2O (500 mL), washed with brine (3×100 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified by a short silica gel column, eluted with 30% ethyl acetate in petroleum ether to give 124 as a brown syrup (18 g, 60%). (ES, m/z) [M+H]+ 461.0; 1H NMR (300 MHz, CDCl3) δ 8.93 (s, 1H), 8.90 (s, 1H), 6.15-6.18 (m, 2H), 4.41-4.45 (m, 1H), 4.28-4.30 (m, 1H), 3.76-4.09 (m, 13H), 3.38 (s, 3H), 3.32 (s, 3H), 3.28 (s, 3H), 3.26 (s, 3H), 1.58 (s, 9H), 1.47 (s, 3H), 1.43 (s, 3H), 1.39 (s, 3H), 1.37 (s, 3H), 1.14-1.21 (m, 6H).

Provenance & Evidence