1-Iodopropane → 1-(2'-Fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)-[1,1'-biphenyl]-2-yl)-2,2-dimethylpentan-1-one

Participants

Reaction Steps

Under a nitrogen atmosphere, to a solution of 1-(2′-fluoro-5′-methoxy-4-((4-methoxybenzyl)oxy)-[1,1′-biphenyl]-2-yl)-2-methylpropan-1-one (128.6 mg) in THF (1574 μL) was added a solution (409 μL) of lithium bis(trimethylsilyl)amide in THF at 0° C., and the mixture was stirred for 10 min. To the reaction mixture was added 1-iodopropane (61.4 μL), and the mixture was stirred at room temperature for 2.5 hr. To the reaction mixture was added, at 0° C., 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 (65.9 mg) as a pale-yellow oil.

Provenance & Evidence