反应详情

Dissolve 5-fluoro-2-nitrobenzaldehyde (9.43 g, 55.81 mmol), 1-butanol (12.41 g, 167.4 mmol) and 4-toluenesulfonic acid monohydrate (0.9 g, 4.7 mmol) in toluene (84 mL). Heat the reaction mixture to reflux, and remove the water using a Dean-Stark apparatus. Continue to heat the reaction mixture for 3 hours. Add water and extract the aqueous layer with ethyl acetate. Combine the organic layers and dry over anhydrous sodium sulfate. Filter, concentrate under reduced pressure and purify by flash column chromatography (1% v/v triethylamine buffered silica gel, 5% ethyl acetate/hexane) to obtain 15.8 g (95%) of the title compound as colorless oil.

1. temperatureHeat the reaction mixture
2. temperatureto reflux
3. customremove the water using a Dean-Stark apparatus
4. temperatureto heat the reaction mixture for 3 hours
5. extractionAdd water and extract the aqueous layer with ethyl acetate
6. dry with materialdry over anhydrous sodium sulfate
7. filtrationFilter
8. concentrationconcentrate under reduced pressure
9. custompurify by flash column chromatography (1% v/v triethylamine buffered silica gel, 5% ethyl acetate/hexane)