Triphenylphosphine → (R)-3-(4-bromo-3,5-dimethylphenoxy)tetrahydrofuran

Participants

Reaction Conditions

Reaction Steps

(S)-Tetrahydrofuran-3-ol 2a (1 g, 11.35 mmol) was dissolved in 30 mL of dichloromethane, followed by addition of 4-bromo-3,5-dimethylphenol (2.28 g, 11.35 mmol). The reaction solution was cooled down to 0° C., followed by addition of triphenylphosphine (3.57 g, 13.62 mmol) and diisopropyl azodicarboxylate (2.75 g, 13.62 mmol) successively. The reaction solution was warmed up to room temperature and stirred for 12 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 (R)-3-(4-bromo-3,5-dimethylphenoxy)tetrahydrofuran 35a (2.27 g, yield 73.9%) as a colorless oil.

Provenance & Evidence