Cyclopentanone → 1-[4-(2-Benzyloxybenzyl)phenyl]-cyclopentanol

Participants

Reaction Steps

In a nitrogen stream, an n-butyllithium hexane solution (1.59 M, 294 mL) was added dropwise to a solution of 1-benzyloxy-2-(4-bromobenzyl)benzene (1.5 g, 4.25 mmol) in THF (16.5 mL) at −78° C. and the mixture was stirred at the same temperature for 30 minutes. To this mixture, a solution of cyclopentanone (357 mg, 4.25 mmol) in THF (4 mL) was added dropwise at −78° C. The reaction mixture was stirred at the same temperature for 50 minutes and at 0° C. for one hour, and then a saturated ammonium chloride aqueous solution was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:10)] to obtain the title compound (1.14 g, 75%) as a colorless oil.

Provenance & Evidence