反应详情

In following a method similar to that described in Katigiri, N; Sato, M.; Yoneda, N.; Saikawa, S.; Sakamoto, T.; Muto, M.; Kaneko, C. J. Chem. Soc. Perkin Trans. 1, 1289-1296, 1986, a solution of 4-benzyloxy-2-pyridone 1 (1.00 g, 5.00 mmol), benzylbromide (4.28 g, 2.97 mL, 25.0 mmol), finely powdered sodium hydroxide (1.00 g, 25.0 mmol), and tetrabutylammonium hydrogen sulfate (0.679 g, 2.00 mmol) in benzene (180 mL) was heated at reflux for 2 h and then cooled to room temperature. The reaction mixture was concentrated and the residue was partitioned between dichloromethane and water. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with water and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a brown solid. This solid was recrystallized from ethyl acetate to afford 1-benzyl-4-benzyloxy-2-pyridone 2 as a tan solid. MS (MH+) 292.2; Calculated 291 for C19H17NO2.

1. temperatureat reflux for 2 h
2. concentrationThe reaction mixture was concentrated
3. customthe residue was partitioned between dichloromethane and water
4. customThe aqueous phase was separated
5. extractionextracted with dichloromethane
6. washThe combined organic phases were washed with water and saturated aqueous sodium chloride solution
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customto afford a brown solid
11. customThis solid was recrystallized from ethyl acetate