Ammonium Chloride → Cyclopentyl(2'-fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)biphenyl-2-yl)methanol

Participants

Reaction Steps

To a mixture of zinc chloride (34 mg), lithium chloride (117 mg) and THF (1 mL) was added a solution (1 M, 0.49 mL) of trimethylsilylmethylmagnesium chloride in diethyl ether, and the mixture was stirred at room temperature for 15 min. To the reaction mixture was added a solution (1 M, 2.7 mL) of cyclopentylmagnesium bromide in THF, and the mixture was stirred at room temperature for 45 min. To the reaction mixture was added a solution of 2′-fluoro-5′-methoxy-4-((4-methoxybenzyl)oxy)biphenyl-2-carbaldehyde (301 mg) obtained in Example 93, step 2, in THF (2 mL) at 0° C., and the mixture was stirred at 0° C. for 1 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, 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 (40 mg) as a colorless oil.

Provenance & Evidence