Imidazole → 1-(4-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)-2-phenylethan-1-one

Participants

Reaction Steps

To a stirring solution consisting of benzyl 4-hydroxyphenyl ketone (650 g) in THF (5.5 L) at room temperature under a nitrogen atmosphere is added tert-butyldimethylsilyl chloride (692 g, 4.59 moles) and imidazole (354 g,). The reaction mixture is stirred overnight and is then concentrated under reduced pressure. The evaporate is dissolved in ether is washed with water and brine, is dried over anhydrous Na2SO4, and is concentrated under reduced pressure to afford a solid. The solid is triturated with pentane. The triturated solids are collected by filtration to afford a solid (850 g.) The filtrate is concentrated under reduced pressure to give a solid. This solid is triturated with pentane and the resulting solids are collected by filtration to provide a second crop of solid (108 g), which afforded a total of 958 g of Compound A.

Provenance & Evidence