Dimethyl Sulfoxide → HCID 59017212, compound

Participants

Reaction Steps

To a stirred solution of oxalyl chloride (0.52 ml; 5.94 mmol) in dry dichloromethane (15 ml) cooled to −78° C. was added a solution of dimethylsulfoxide (0.81 ml, 11.42 mmol) in dry dichloromethane (2 ml). Stirring was continued for 10 minutes followed by dropwise addition of a solution of the material (1 g) prepared in Example 25 (4.57 mmol) in dry dichloromethane (10 ml). The mixture was stirred for a further 15 minutes then triethylamine (3.8 ml; 27.3 mmol) was added. After stirring at −78° C. for a further 10 minutes the mixture was allowed to warm to 0° C. before ethyl acetate (50 ml) and water (50 ml) were added. After thorough mixing the organic layer was separated, washed sequentially with 1M HCl (50 ml) and brine (50 ml), and dried (Na2SO4). The solvent was removed under reduced pressure and the residue purified by flash chromatography eluting with 3% MeOH in methylene chloride to give the title product (220 mg) which was recrystallised once from the minimum of hot ethyl acetate, 1H NMR (CDCl3) δ 2.41 (dd, 1H), 2.87-2.93 (m, 1H), 4.15-4.33 (m, 3H), 4.45-4.49 (m, 2H), 7.06 (d, 1H), 7.18 (t, 1H), 7.44 (dd, 1H), 8.03 (dd, 1H); EIMS: m/z =218.4 [M+H]+

Provenance & Evidence