反应详情

温度

-50 °C

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.

1. customdid not exceed −35° C
2. extractionthereto followed by extraction with ethyl acetate
3. washThe organic layer was washed with water
4. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate
5. distillationAfter distilling off the solvent under reduced pressure, 23.82 g of a pale yellow oily substance
6. customwas obtained
7. custom13.82 g of this oily substance was purified by silica gel column chromatography (eluted with dichloromethane/methanol)