m-Chloroperbenzoic acid → HCID 18385842, compound

Participants

Reaction Conditions

Reaction Steps

To 320 mg of 4-(3,5-difluorophenyl)-2,2-dimethyl-5-{3-methyl-4-(methylthio)phenyl}-3(2H)-furanone (Example 381) in 50 ml dichloromethane, was added 172 mg of 70% m-chloroperoxybenzoic acid. The mixture was stirred at 0° C. for an hour, which was followed by addition of 30 ml 5% aqueous sodium bicarbonate. The solution was stirred for another 10 minutes. Then the mixture was concentrated in vacuo, and was extracted with 50 ml water and dichloromethane (30 ml×3). Then the organic layer was concentrated under reduced pressure and was purified by column chromatography (hexane/ethylacetate=1:1) to give 211 mg of 4-(3,5-difluorophenyl)-2,2-dimethyl-5-{3-methyl-4-(methylsulfinyl)phenyl}-3(2H)-furanone. NMR: δ1.57 (s, 6H), 2.36 (s, 3H), 2.73 (s, 3H), 6.77 (m, 1H), 6.86 (m, 2H), 7.50 (m, 1H), 7.66 (m, 1H), 7.99 (d, J=8.4 Hz, 1H). IR (cm−1): 1698,1624,1592,1384, 1310,1206,1072,915.

Provenance & Evidence