Water → HCID 53699781, compound

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.

1. stirringThe mixture was stirred for 1.5 hours
2. stirringstirred overnight at a room temperature
3. customthe resulting layers were separated
4. extractionthe aqueous solution was extracted with 20 ml of n-hexane
5. washwashed with water
6. dry with materiala saturated sodium chloride aqueous solution, dried over magnesium sulfate
7. customevaporated under a reduced pressure
8. customto obtain an oily residue
9. washeluted with n-hexane/ethyl acetate (50:1)

ORD record

ord-e8a2cc99c0e44d67879d583488d9d65f

Source dataset

uspto-grants-1992_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05093370