Tributylphosphine → HCID 86588415, compound

Participants

Reaction Steps

Under a atmosphere of nitrogen, azodicarboxylic dipiperidide (0.91 g, 3.62 mmol) was added at 0–5° C. to a stirred solution of tributylphosphine (0.89 mL, 3.62 mmol), (S)-ethyl 2-ethoxy-3-(4-hydroxyphenyl)-propionate (0.60 g, 2.53 mmol) and (E)(E) 3-(4′-{3-[(tert-butyidimethylsilanyl)-methoxy]-1-methylpropenyl}-biphenyl-4-yl)-but-2-en-1-ol (1.02 g, 2.41 mmol) in dry THF (15 ml). The mixture was warmed to room temperature, and stirred for 18 h. The resulting mixture was diluted with water and ethyl acetate, the aqueous layer collected and further extracted with ethyl acetate. The organic layers were combined, washed with brine, dried (MgSO4) and evaporated. The crude product was then purified by column chromatography on silica using heptane/ethyl acetate (4:1) as eluent to give 1.18 g (76%) of (E)(E)(S) 3-{4-[3-(4′-{3-[(tert-butyldimethylsilanyl)-methoxy]-1-methylpropenyl}-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acid ethyl ester.

Provenance & Evidence