Water → (2'-Fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)-[1,1'-biphenyl]-2-yl)methyl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

Methanesulfonyl chloride (0.164 mL) was added to a solution of (2′-fluoro-5′-methoxy-4-((4-methoxybenzyl)oxy)-[1,1′-biphenyl]-2-yl)methanol (390 mg) in THF (10 mL) at 0° C., and the mixture was stirred at 0° C. for 20 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give (2′-fluoro-5′-methoxy-4-((4-methoxybenzyl)oxy)-[1,1′-biphenyl]-2-yl)methyl methanesulfonate. To solution (10 mL) of the obtained compound and TBAI (117 mg) in DMF was added sodium hydride (60%, 85 mg) at 0° C., and the mixture was stirred at 0° C. for 5 min, then at 80° C. for 5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (326 mg) as a colorless oil.

Provenance & Evidence