Methanol → 5-[2-Fluoro-4-(methylsulfonyl)phenyl]-2,2-dimethyl-4-phenyl-3(2H)-furanone

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Reaction Steps

305 mg of 2,2-dimethyl-5-{2-fluoro-4-(methylthio)phenyl}-4-phenyl-3(2H)-furanone (Example 314) was dissolved in 30 ml methanol, 20 ml TBF and 20 ml water, to which 1.4 g of OXONE was added. The reaction mixture was stirred overnight at room temperature. Then the solvent was removed in vacuo and 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 chromatography (hexane/acetate=3:2) to obtain 70 mg of 2,2-dimethyl-5-{2-fluoro-4-(methylsulfonyl)phenyl}-4-phenyl-3(2H)-furanone as a solid. mp: 175-176° C. NMR: δ1.57 (s, 6H), 3.10 (s, 3H), 7.22 (m, 2H), 7.28 (m, 3H), 7.75 (dd, J=8.7, 1.8 Hz, 1H), 7.77 (m, 2H). IR (cm−1): 1702, 1408, 1321, 1147. MS (FAB): 361 (m+1).

Provenance & Evidence