反应详情

温度

-75 °C

Butyllithium (47.5 ml of 2.22M solution, 106 mmol) was added slowly to a solution of pentamethyldiethylenetriamine (15 ml) and 4-fluoroanisole (12.61 g, 0.1 mol) in THF (150 ml) at -70° C. The solution was stirred for 2 hr at -75° C. and a solution of pyridine-4-carboxaldehyde (9.55 ml, 0.1 mol) in THF was added at -75° C. The mixture was allowed to warm to 25° C. slowly and then quenched with ammonium chloride solution. The mixture was diluted with ethyl acetate and the organic layer was separated. The organic layer was washed with water and 3N hydrochloric acid. The acid washes were then basified with sodium hydroxide and extracted with ether and the ether solution concentrated in vacuo. The crude product was recrystallized from 80% ethanol to give (2-fluoro-5-methoxy-phenyl)-4-pyridylmethanol as a white powder (12.22 g+3.12 g second crop, 66% total yield).

1. temperatureto warm to 25° C. slowly
2. customquenched with ammonium chloride solution
3. additionThe mixture was diluted with ethyl acetate
4. customthe organic layer was separated
5. washThe organic layer was washed with water and 3N hydrochloric acid
6. extractionextracted with ether
7. concentrationthe ether solution concentrated in vacuo
8. customThe crude product was recrystallized from 80% ethanol
9. customto give