反应详情

To an aqueous solution (100 mL) of 2-chloro-5-hydroxypyridine (10.0 g) were added sodium carbonate (16.3 g) and iodine (10.8 g), and the mixture was stirred at room temperature for 5 days. The reaction mixture was acidified to pH=5 with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a yellow solid. The obtained solid was recrystallized from methanol to give a brown solid. To a solution (200 mL) of the obtained solid in acetone were added benzyl bromide (8.02 mL) and potassium carbonate (15.5 g), and the mixture was stirred overnight with heating under reflux. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-30% ethyl acetate/hexane) to give the title object compound (18.4 g, 69%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ ppm 5.17 (s, 2H), 6.97 (d, J=8.4 Hz, 1H), 7.15 (d, J=8.4 Hz, 1H), 7.30-7.47 (m, 5H).

1. extractionthe mixture was extracted with ethyl acetate
2. washThe extract was washed with saturated brine
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. customto give a yellow solid
6. customThe obtained solid was recrystallized from methanol
7. customto give a brown solid
8. stirringthe mixture was stirred overnight
9. temperaturewith heating
10. temperatureunder reflux
11. filtrationInsoluble material was filtered off
12. concentrationthe filtrate was concentrated under reduced pressure
13. customThe residue was purified by silica gel column chromatography (0-30% ethyl acetate/hexane)