反应详情

6.97 g of 4-methoxy-2-methylpyridine was dissolved in 200 ml of acetone and 13.5 g of benzyl bromide was added thereto. Then the resulting mixture was heated under reflux for 2 hours and 30 minutes. The reaction mixture was cooled to room temperature and diluted with diethyl ether. The precipitate was taken up by filtration and the solid matter was dissolved in 60 ml of water. Next, 5.35 g of sodium borohydride was added thereto in portions. After stirring for 15 minutes, the reaction mixture was concentrated under reduced pressure, diluted with ethyl acetate, washed successively with water and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure. To the obtained residue was added 5 N hydrochloric acid and the resulting mixture was stirred at room temperature overnight. The reaction mixture was made basic by adding potassium carbonate, extracted with ethyl acetate, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 6.84 g of the title compound as a colorless oily substance.

1. temperatureThen the resulting mixture was heated
2. temperatureunder reflux for 2 hours and 30 minutes
3. filtrationThe precipitate was taken up by filtration
4. dissolutionthe solid matter was dissolved in 60 ml of water
5. additionNext, 5.35 g of sodium borohydride was added
6. concentrationthe reaction mixture was concentrated under reduced pressure
7. additiondiluted with ethyl acetate
8. washwashed successively with water
9. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
10. filtrationAfter filtration
11. distillationthe solvent was distilled off under reduced pressure
12. additionTo the obtained residue was added 5 N hydrochloric acid
13. stirringthe resulting mixture was stirred at room temperature overnight
14. additionby adding potassium carbonate
15. extractionextracted with ethyl acetate
16. washwashed with a saturated aqueous solution of sodium chloride
17. dry with materialdried over anhydrous magnesium sulfate
18. filtrationAfter filtration
19. distillationthe solvent was distilled off under reduced pressure
20. customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)