反应详情

温度

5 °C

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.

1. temperaturethe suspension was warmed to room temperature
2. temperatureIt was cooled to −78° C.
3. temperaturethe mixture was warmed to room temperature
4. stirringstirred for 2.5 hours
5. customthe organic layer was separated
6. washwashed with brine
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. customThe filtrate was evaporated to dryness
10. customthe residue was purified by chromatography on silica
11. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 15-35%