HCID 18385936, compound → HCID 18385659, compound

Participants

Reaction Steps

1.2 g of 5-{3-chloro-4-(methylthio)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone (Example 354) was dissolved in 150 ml of 1:1:1 methanol/THF/water, to which was added 2.8 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 50 ml water and ethylacetate (100 ml×3). The organic layer was concentrated in vacuo and was purified by column chromatography hexane/ethylacetate=3:1) to give 1.1 g of 5-{3-chloro-4-(methylsulfonyl)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone as a solid. mp: 174-175° C. NMR: δ1.58 (s, 6H), 3.28 (s, 3H), 7.27 (m, 3H), 7.39 (m, 2H), 7.66 (dd, J=8.4, 1.8 Hz, 1H), 7.86 (d, J=1.8 Hz, 1H), 8.09 (d, J=8.4 Hz, 1H). IR (cm−1): 1700, 1587, 1391, 1321, 1241, 1152.

Provenance & Evidence