反应详情

2-hydroxymethyl-3-hydroxypyridine (100.3 g, 620.7 mmol) was dissolved in acetone (1 L). Potassium carbonate (180 g, 1.3 mol) was added followed by benzyl bromide (127 g, 745 mmol). The mixture was heated at reflux for 48 hours. The resultant mixture was cooled to room temperature and filtered through celite. The filter cake was washed with acetone (1 L). The combined filtrate was concentrated in vacuo to provide an orange oil. This oil was purified by silica gel column chromatography using 10-40% ethyl acetate/hexanes as eluant. The resultant tan solid was recrystallized from hexanes to provide the product (88.2 g, 66% yield). 1H NMR (400 MHz, CDCl3) δ 8.2 (t, 1H), 7.4 (m, 5H), 7.15 (d, 2H), 5.1 (s, 2H), 4.8 (d, 2H), 4.3 (t, 1H).

1. temperatureThe mixture was heated
2. temperatureat reflux for 48 hours
3. filtrationfiltered through celite
4. washThe filter cake was washed with acetone (1 L)
5. concentrationThe combined filtrate was concentrated in vacuo
6. customto provide an orange oil
7. customThis oil was purified by silica gel column chromatography
8. customThe resultant tan solid was recrystallized from hexanes