Sodium Hydroxide → HCID 18385668, compound

Participants

Reaction Steps

391 mg of 5-{3-bromo-4-(methylthio)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone (Example 336) dissolved in 50 ml dichloromethane was stirred at 0° C. for 50 minutes in the presence of 183 mg of 70% m-chloroperoxybenzoic acid. Then 10 ml 5% aqueous sodium hydroxide was added to the reaction mixture and the mixed solution was stirred for another 10 minutes. The dichloromethane was removed in vacuo and the resulting residue was extracted with 50 ml water and dichloromethane (30 ml×3). The organic layer was then concentrated under reduced pressure and was purified by column chromatography (hexane/ethylacetate=1:1) to give 310 mg of 5-(3-bromo-4-(methylsulfinyl)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone. NMR: δ1.58 (s, 6H), 2.84 (s, 3H), 7.30 (m, 2H), 7.38 (m, 3H), 7.78 (dd, J=8.4, 1.8 Hz, 1H), 7.88 (d, J=5.4 Hz, 1H), 7.90 (d, J=2.7 Hz, 1H). IR (cm−1): 1698, 1619, 1388, 1064.

Provenance & Evidence