Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (2S)-3-(2,4-Difluorophenyl)-3-buten-2-ol

Participants

Reaction Conditions

Reaction Steps

A mixture of compound 5a, (3S)-2-(2,4-Difluorophenyl)-3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-1-butene, (81 g, 0.302 mole) and pyridinium-p-toluenesulfonate (32.7 g, 0.130 mole) in 1200 ml of ethanol was heated at 60° C. for 9 hours. The reaction mixture was concentrated in vacuo and co-evaporated with toluene. Toluene was then added to the residue and the resulting solid was removed by filtration. The filtrate was evaporated under reduced pressure and the residue was chromatographed on silica gel. Elution with 10% ethyl acetate in hexane gave the title compound 6a as light yellow oil (44.96 g, 81%)

Provenance & Evidence