HCID 18385789, compound → HCID 18385602, compound

Participants

Reaction Steps

350 mg of 5-{2-chloro-4-(methylthio)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone (Example 387) was dissolved in 75 ml of 1:1:1 methanol/THF/water, to which was added 1.0 g of OXONE. The reaction mixture was stirred at room temperature for 6 hours. The reaction mixture was concentrated in vacuo and the resulting residue was extracted with 25 ml water and ethylacetate (50 ml×3). The organic layer was concentrated in vacuo and was purified by column chromatography (hexane/ethylacetate=3:1) to give 252 mg of 5-{2-chloro-4-(methylsulfonyl)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone as a solid. mp: 89-90° C. NMR: δ1.59 (s, 6H), 3.11 (s, 3H), 7.19 (m, 2H), 7.25 (m, 3H), 7.60 (d, J=8.1 Hz, 1H), 7.87 (dd, J=8.1, 1.8 Hz, 1H), 8.07 (d, J=1.8 Hz, 1H). IR (cm−1): 1701, 1625, 1586, 1391, 1319, 1153.

Provenance & Evidence