Ethyl Acetate → Methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-(2-vinylfuran-3-yl)-benzoate

Participants

Reaction Conditions

Reaction Steps

A suspension of methyltriphenylphosphonium bromide (pre-dried under vacuum at 60° C., 3.80 g) in THF (60 mL) was cooled to 5° C., under nitrogen. Potassium bis-(trimethylsilyl)amide (0.5M in toluene, 21.3 mL) was added and the suspension was warmed to room temperature and stirred for 45 minutes. It was cooled to −78° C. and a solution of methyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-hydroxybenzoate (Intermediate 28, 1.42 g) in THF (40 mL) was added and the mixture was warmed to room temperature and stirred for 2.5 hours. Ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the mixture and the organic layer was separated, washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 15-35% to give methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-(2-vinylfuran-3-yl)-benzoate (1.24 g) as a white solid.

Provenance & Evidence