Triphenylphosphine → 3-[4-((S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propoxy)-phenyl]-propionic acid methyl ester

Participants

Reaction Steps

To 320 mg (0.6 mmol) of (S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propan-1-ol in 5 mL of THF were added 0.14 g (0.8 mmol) of 3-(4-hydroxy-phenyl)-propionic acid methyl ester and 0.2 g (0.8 mmol) of triphenylphosphine. The mixture was cooled to 0°, was treated with 0.12 mL (0.8 mmol) of DEAD and was stirred at room temperature overnight. A solution of NH4Cl was added, the phases were separated and the inorganic one was extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4), filtered and evaporated. The crude product was purified by column chromatography on silica gel with EtOAc/n-heptane 1:3 to yield 330 mg (79%) of 3-[4-((S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propoxy)-phenyl]-propionic acid methyl ester as a yellow oil.

Provenance & Evidence