Tributylphosphine → Ethyl 3-(2-fluoro-4-{[4-(1-hydroxybutyl)benzyl]oxy}phenyl)propanoate

Participants

Reaction Steps

A solution of ethyl 3-(2-fluoro-4-hydroxyphenyl)propanoate (2.12 g, 10.0 mmol), 1-[4-(hydroxymethyl)phenyl]-butane-1-ol (1.80 g, 10.0 mmol) and tributylphosphine (4.04 mL, 20.0 mmol) in toluene (150 mL) was stirred under ice-cooling and 1,1′-(azodicarbonyl)dipiperidine (5.04 g, 20.0 mmol) was added by small portions. The mixture was warmed to room temperature and stirred for 22 hr. Hexane (75 mL) was added to the reaction mixture, and precipitated insoluble material was filtered off. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-30:70) to give the title compound as a colorless oil (1.93 g, yield 52%).

Provenance & Evidence