Cornforth reagent → 4-Hydroxy-4-methyl-1-{4-(methylthio)phenyl}-2-hexyn-1-one

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Reaction Steps

To 9.9 g of 4-methyl-1-{4-(methylthio)phenyl}-2-hexyn-1,4-diol dissolved in 200 ml dichloromethane, were added 15 g of pyridinium dichromate (PDC) and 15 g of celite. The suspension was stirred overnight at room temperature, and then the insoluble material was filtered off through Florisil. The filtrate was purified by column chromatography (hexane/ethylactate=4:1) to give 5.34 g of 4-hydroxy-4-methyl-1-{4-(methylthio)phenyl}-2-hexyn-1-one. NMR: δ1.13 (t, J=7.5 Hz, 3H), 1.62 (s, 3H), 1.85 (q, J=7.8 Hz, 2H), 2.54 (s, 3H), 7.28 (d, J=8.7 Hz, 2H), 8.01 (d, J=8.7 Hz, 2H). IR (cm−1): 3427, 2974, 1588, 1095, 914, 745.

Provenance & Evidence