Water → HCID 53699781, compound

Participants

Reaction Steps

First, 207 mg of metalic sodium was dissolved in 4 ml of absolute ethanol, and the ethanol was evaporated off to obtain sodium ethoxide powder, to which was then added at once a solution of 4.75 g ethoxycarbonylpropyltriphenylphosphonium bromide in 15 ml of absolute dimethylformamide with stirring. The mixture was stirred for 1.5 hours, and after adding dropwise a solution of 1.04 g 4-phenylbutylaldehyde in 5 ml of absolute dimethylformamide at 5° C. over 5 minutes, stirred overnight at a room temperature. To the reaction mixture were added 100 ml of n-hexane and 30 ml of water and the resulting layers were separated, and the aqueous solution was extracted with 20 ml of n-hexane. The n-hexane layers were combined, washed with water and a saturated sodium chloride aqueous solution, dried over magnesium sulfate and evaporated under a reduced pressure to obtain an oily residue. The residue was applied to a silica gel column and eluted with n-hexane/ethyl acetate (50:1) to obtain 831 mg of the title compound as a colorless liquid.

Provenance & Evidence