反应详情

温度

0 °C

n-Butyllithium (38.7 mL; 10 M in tetrahydrofuran (THF)) was dissolved in THF (600 mL) and cannulated to a solution of 2,3-dimethoxypyridine (3) (22.4 g; 161 mmol) in THF (200 mL) at −78° C. The reaction mixture was then warmed to 0° C. and stirred for 1 hour. The propionaldehyde (29.1 mL; 403 mmol) was added dropwise at −78° C. The reaction mixture was warmed to 25° C. and stirred for 16 hours. The reaction mixture was subsequently quenched with water and extracted with dichloromethane. The combined extracts were dried over sodium sulfate, concentrated under reduced pressure and purified by chromatography (SiO2; 2-10% ethyl acetate/hexane) to give the 2,3-dimethoxy-4-(1′-hydroxypropyl)pyridine (4) product (18.6 g; 59%) as a colorless oil.

1. temperatureThe reaction mixture was warmed to 25° C.
2. stirringstirred for 16 hours
3. customThe reaction mixture was subsequently quenched with water
4. extractionextracted with dichloromethane
5. dry with materialThe combined extracts were dried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. custompurified by chromatography (SiO2; 2-10% ethyl acetate/hexane)