m-Chloroperbenzoic acid → HCID 18385610, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution 2.7 g of 5-{2-chloro-4-(methylthio)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone (Example 387) in 80 ml dichloromethane, was added 1.94 g of 70% m-chloroperoxybenzoic acid. 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 978 mg of 5-{2-chloro-4-(methylsulfinyl)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone as a solid. mp: 135-136° C. NMR: δ1.59 (s, 6H), 2.78 (s, 3H), 7.22 (m, 3H), 7.25 (m, 2H), 7.54 (m, 2H), 7.79 (m, 1H). IR (cm−1): 1698, 1623, 1392, 1242, 1145, 1063.

Provenance & Evidence