HCID 17756279, compound → HCID 17756175, compound

Participants

Reaction Steps

To a stirring cooled (0° C.) solution of 4-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-benzoic acid methyl ester (0.80 g, 2.48 mol) in THF (5.5 mL) was added dropwise a solution of lithium aluminum hydride (4.96 mL, 1M in THF). After completion of addition the reaction mixture continued to stir at room temperature. After 2 hours, the reaction mixture was quenched with water. The aqueous layer was extracted with ethyl acetate. All combined organic layers were dried over Na2SO4, filtered, and concentrated to yield a yellow oil. The crude material was purified using silica gel chromatography (1:2 ethyl acetate:hexanes) to afford {4-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-phenyl}-methanol (0.65 g, 2.21 mol, 89% yield).

Provenance & Evidence