Bromide ion → HCID 23021535, compound

Participants

Reaction Conditions

Reaction Steps

5.66 g of cyclopentyltriphenylphosphonim bromide was suspended in 25 mL of diethyl ether, to which 8.8 mL of a solution of n-butyllithium in n-hexane (1.56 M) was added dropwise at −30° C. After the reaction mixture was stirred for one hour at 5° C., 2.67 g of 3-(benzyloxy)benzaldehyde dissolved in 5 mL of diethyl ether was added to the reaction mixture, which was then stirred another one hour at room temperature. The reaction mixture was added to a mixture of methylene chloride and dilute hydrochloric acid, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1] to yield 1.06 g of 1-(benzyloxy)-3-(cyclopentylidenemethyl)benzene as light yellow solid.

Provenance & Evidence