m-Chloroperbenzoic acid → HCID 11767461, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred cooled (-78° C.) solution of 3 (130 g, 0.2 mol) in dichloromethane (400 mL) is added dropwise over a period of 20 min a solution of mCPBA (74%, 58.31 g, 0.25 mol) in dichloromethane (300 mL). The mixture is stirred and allowed to warm up to -30° C. The mixture is then filtered. The filtrate is washed with saturated aqueous sodium bisulfite (2×300 mL), sodium bicarbonate (2×400 mL), brine (400 mL) and water (2×400 mL). The organic layer is dried (Na2SO4) and concentrated. Flash chromatography (CH2Cl2 :EtOAC=9:1) of the residue furnishes sulfoxide mixture 4 (127 g, 95%) as a white solid (mp 120°-122° C.). TLC Rf =0.3 (solvent--EtOH:CH2Cl2 =1:9). IR (KBr): 3060, 3030, 2910, 2867, 1495, 1450, 1360, 1210, 1136, 1092, 1049 cm-1. 1H NMR (CDCl3): 7.72-7.14 (m, 25H), 5.12-4.42 (m, 9H), 4.40-3.30 (m, 6H). Anal. Calc. for C40H40O6S: C, 74.04; H, 6.22; S, 4.93. Found: C, 74.10; H, 6.26; S, 4.99.

Provenance & Evidence