Triphenylphosphine → Ethyl 3-[4-({2',6'-dimethyl-4'-[(6-methylpyridin-2-yl)methoxy]biphenyl-3-yl}methoxy)-2-fluorophenyl]propanoate

Participants

Reaction Steps

To a solution of ethyl 3-{2-fluoro-4-[(4′-hydroxy-2′,6′-dimethylbiphenyl-3-yl)methoxy]phenyl}propanoate (1.2 g, 2.84 mmol), (6-methylpyridin-2-yl)methanol (0.39 g, 3.12 mmol) and triphenylphosphine (0.95 g, 3.61 mmol) in tetrahydrofuran (24 mL) was added diisopropyl azodicarboxylate (40% toluene solution, 1.54 mL, 3.12 mmol) at room temperature with stirring. The reaction mixture was stirred at room temperature for 12 hrs., and an equivalent amount of the aforementioned reagents ((6-methylpyridin-2-yl)methanol, triphenylphosphine and diisopropyl azodicarboxylate) were added. The mixture was further stirred at the same temperature for 12 hrs. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=1/1) to give the title compound (1.3 g, yield 87%) as a colorless oil.

Provenance & Evidence