反应详情

温度

0 °C

Sodium (1.22 g, 52.9 mmol, 2.1 eq) is added portionwise at 0° C. to a stirred solution of allyl alcohol (117.1 g, 201.6 mmol, 80.0 eq). After 30 minutes stirring at 0° C., 4-bromo-6-methoxy-quinoline (6.0 g, 25.2 mmol, 1.0 eq) is added to the reaction mixture that is heated under reflux for 5 hours. The reaction mixture is then cooled down to room temperature, and filtered. The filtrate is evaporated under reduced pressure to give a residue that is extracted with ethyl acetate (3×100 mL) and water (100 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 60:1, v/v) to afford 4-allyloxy-6-methoxy-quinoline as a white solid (4.0 g, 74% yield).

1. temperatureis heated
2. temperatureunder reflux for 5 hours
3. temperatureThe reaction mixture is then cooled down to room temperature
4. filtrationfiltered
5. customThe filtrate is evaporated under reduced pressure
6. customto give a residue that
7. extractionis extracted with ethyl acetate (3×100 mL) and water (100 mL)
8. dry with materialThe combined organic layers are dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customto give a crude product that
12. customis purified by column chromatography (silica gel, eluent