Water → HCID 18385921, compound

Participants

Reaction Steps

350 mg of 5-{3-bromo-4-(methylthio)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone (Example 336), dissolved in 50 ml methanol, 50 ml THF and 50 ml water, was reacted with 1.5 g of OXONE by stirring at room temperature for 15 hours. 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 was purified by column chromatography (hexane/ethylacetate=3:2) to yield 173 mg of 5-{3-bromo-4-(methylsulfonyl)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone as a solid. mp: 154-155° C. NMR: δ1.58 (s, 6H), 3.29 (s, 3H), 7.26 (m, 3H), 7.38 (m, 2H), 8.07 (d, J=1.8 Hz, 1H), 8.10 (d, J=8.1 Hz, 2H). IR (cm−1): 1698, 1585, 1318, 1150.

Provenance & Evidence