Water → HCID 18670147, compound

Participants

Reaction Conditions

Reaction Steps

15.0 g of 4-bromo-2-methoxybenzaldehyde dimethyl acetal was dissolved in 150 ml of ether and the obtained solution was cooled to −50° C. Then 25.3 ml of a 1.6 M solution of n-butyllithium in hexane was dropped thereinto. 1 hour thereafter, 30 ml of a solution of 11.7 ml of 1-benzyl-4-piperidone in diethyl ether was dropped thereinto in such a manner that the bulk temperature did not exceed −35° C. After stirring at room temperature for 50 minutes, water was added thereto followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, 23.82 g of a pale yellow oily substance was obtained. 13.82 g of this oily substance was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 6.31 g of the title compound as a pale yellow solid.

Provenance & Evidence