Triphenylphosphine → methyl 2-((S)-6-((2,2',6'-trimethyl-4'-(((S)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

Participants

Reaction Conditions

Reaction Steps

(S)-(2,2′,6′-Trimethyl-4′-((tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methanol 12e (75 mg, 0.24 mmol), methyl (S)-2-(6-hydroxyl-2,3-dihydrobenzofuran-3-yl)acetate (50 mg, 0.24 mmol) and triphenylphosphine (94 mg, 0.36 mmol) were dissolved in 20 mL of dichloromethane. The reaction solution was cooled down to 0° C., followed by addition of diisopropyl azodicarboxylate (73 mg, 0.36 mmol), then warmed up to room temperature and stirred for 2 hours. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography with elution system B to obtain the title compound methyl 2-((S)-6-((2,2′,6′-trimethyl-4′-(((S)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 12f (100 mg, yield 83.0%) as a white solid.

Provenance & Evidence