m-Chloroperbenzoic acid → HCID 18385651, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution 3.5 g of 5-{3-chloro-4-(methylthio)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone (Example 354) in 80 ml dichloromethane, was added 2.5 g of 70% m-chloroperoxybenzoic acid, and the reaction mixture was stirred at 0° C. for 2 hours. Then 40 ml 5% aqueous sodium bicarbonate was added to the solution and the solution was stirred for 10 minutes. The solution was extracted with dichloromethane (50 ml×3). The organic layer was concentrated in vacuo and was purified by column chromatography (hexane/ethylacetate=1:1) to give 2.43 g of 5-{3-chloro-4-(methylsulfinyl)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone as a solid. mp: 120-121° C. NMR: δ1.57 (s, 6H), 2.84 (s, 3H), 7.30 (m, 3H), 7.38 (m, 2H), 7.72 (s, 1H), 7.74 (d, J=8.1 Hz, 1H), 7.91 (d, J=8.1 Hz, 1H). IR (cm−1): 1699, 1619, 1319, 1239, 1169, 1145, 1068.

Provenance & Evidence