反应详情

温度

100 °C

To a solution of 6-fluoropyridin-3-ol (75 g, 663 mmol) in DMF (265 mL, 663 mmol) were added potassium carbonate (59.7 g, 995 mmol) and iodomethane (108 g, 763 mmol). The resulting slurry was heated at 100° C. for 3 hours. The reaction was diluted with water (1000 mL) and poured into a separatory funnel containing diethyl ether (1000 mL). The layers were separated and the aqueous layer was extracted with diethyl ether (4×500 mL). The combined organic layers were washed with water and then brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide a yellow oil. This oil was diluted with 500 mL of DCM and concentrated to provide a yellow oil with a large amount of an off white precipitate. The mixture was filtered and the derived solid was washed well with DCM. The filtrate was concentrate to provide a mixture consisting of a yellow oil and an off white solid. The solid was filtered, washing with DCM. Repeat this procedure again and then concentrated the filtrate to provide a yellow oil. The oil was taken up in 100 mL of ether and flashed through a plug of silica gel with 10:1 hexanes:ether to provide 2-fluoro-5-methoxypyridine as a yellow oil.

1. additionpoured into a separatory funnel
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with diethyl ether (4×500 mL)
4. washThe combined organic layers were washed with water
5. dry with materialbrine, dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto provide a yellow oil
9. concentrationconcentrated
10. customto provide a yellow oil with a large amount of an off white precipitate
11. filtrationThe mixture was filtered
12. washthe derived solid was washed well with DCM
13. concentrationThe filtrate was concentrate
14. customto provide a mixture
15. filtrationThe solid was filtered
16. washwashing with DCM
17. concentrationRepeat this procedure again and then concentrated the filtrate
18. customto provide a yellow oil