反应详情

Hydrogen peroxide (20.9 ml, 0.61453 moles, Baker) and acetic acid (125 ml, Baker) were combined and stirred at room temperature (RT). The 3-acetylpyridine (50 ml, 0.40984 moles, Aldrich), distilled prior to use (94° C., 2.00 mm Hg), was added and then, the reaction mixture was stirred overnight (O/N) at 95° C. Next, the reaction mixture was cooled to RT and then, neutralized with saturated K2CO3 (400 ml). Then, 5 g of KSO3 was added to destroy the remaining hydrogen peroxide. Next, methanol (750 ml) was added and the resultant cloudy solution was filtered. The filtrate was then evaporated to dryness using a rotary evaporator. The semi-solid was extracted repeatedly with hot CH2Cl2 (4×500 ml) and combined. Next, the solvent was removed leaving approximately 44 g of a crude, pale yellow solid. The crude solid was dissolved in hot 2-propanol (150 ml) and stirred until cool in an icebath. The white solid which precipitated was collected, washed with 2-propanol (100 ml) and dried in a vacuum dessicator O/N at 50° C. The air-dried weight was 41 g. HPLC analysis of the recrystallized sample (m.p. 146°-147° C.) showed a single principal peak 96% by area.

1. custom(94° C., 2.00 mm Hg)
2. additionwas added
3. stirringthe reaction mixture was stirred overnight (O/N) at 95° C
4. temperatureNext, the reaction mixture was cooled to RT
5. customto destroy the remaining hydrogen peroxide
6. additionNext, methanol (750 ml) was added
7. filtrationthe resultant cloudy solution was filtered
8. customThe filtrate was then evaporated to dryness
9. customa rotary evaporator
10. extractionThe semi-solid was extracted repeatedly with hot CH2Cl2 (4×500 ml)
11. customNext, the solvent was removed
12. customleaving approximately 44 g of a crude, pale yellow solid
13. stirringstirred
14. temperatureuntil cool in an icebath
15. customThe white solid which precipitated
16. customwas collected
17. washwashed with 2-propanol (100 ml)
18. customdried in a vacuum dessicator O/N at 50° C