m-Chloroperbenzoic acid → HCID 18385736, compound

Participants

Reaction Conditions

Reaction Steps

To 241 mg of 2,2-dimethyl-5-{2-fluoro-4-(methylthio)phenyl}-4-phenyl-3(2H)-furanone (Example 314) dissolved in 50 ml dichloromethane, was added 138 mg of 70% m-chloroperoxybenzoic acid. The mixture was stirred at 0° C. for 1.5 hours, which was followed by addition of 30 ml 5% aqueous sodium bicarbonate. Then the mixture was stirred for 10 minutes and the volatile material was removed in vacuo. The resulting residue was extracted with 50 ml water and dichloromethane (30 ml×3). The organic layer was concentrated under reduced pressure, and then was purified by column chromatographic separation (hexane/ethylacetate=1:1) to afford 187 mg of 2,2-dimethyl-5-{2-fluoro-4-(methylsulfinyl)phenyl}-4-phenyl-3(2H)-furanone as a solid. mp: 149-150° C. NMR: δ1.55 (s, 6H), 2.78 (s, 3H), 7.26 (m, 5H), 7.47 (m, 2H), 7.69 (dd, J=8.4, 6.6 Hz, 2H). IR (cm−1): 1700, 1621, 1380, 1223, 1161, 1075.

Provenance & Evidence