Cerium(III) chloride → HCID 18385745, compound

Participants

Reaction Steps

A mixture of 4-(4-acetylphenyl)-2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone (150 mg, Example 10), sodium borohydride(35mg) and cerium(III) chloride (20 mg) in 40 ml methaol was stirred at room temperature for 12 hours, which was followed by addition of water. Then the methanol was removed in vacuo and the resulting aqueous solution was extracted with ethylacetate. The ethylacetate layer was concentrated under reduced pressure and was purified by column chromatography (hexane/ethylacetate=1:1) to obtain 100 mg of 2,2-dimethyl-4-{4-(1-hydroxyethyl)phenyl}-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone. NMR: δ1.51-1.53 (d, J=6.3 Hz, 3H), 1.58 (s, 6H), 3.07 (s, 3H), 4.90-4.97 (q, J=6.3 Hz, 1H), 7.25-7.28 (m, 2H), 7.39-7.42 (m, 2H), 7.84-7.86 (m, 2H), 7.92-7.95 (m, 2H). IR (cm−1): 3502, 2977, 1696, 1594, 1317, 1149 960, 771.

Provenance & Evidence