反应详情

The title compound was prepared by the method of Dauzonne, D.; Demerseman, P. Synthesis 1990, 66-70. Benzaldehyde 158 (3.59 g, 33.8 mmol), bromonitromethane 159 (9.0 g, 64.3 mmol), dimethylamine hydrochloride (24.8 g, 304.2 mmol), potassium fluoride (spray-dried, 0.3 g, 5.08 mmol) and m-xylenes (85 mL) were combined in a 250 mL round bottom flask. The flask was then connected to a Dean-Stark trap and reflux condenser and the mixture was heated at reflux with azeotropic removal of water for 24 h. After cooling to room temperature, the reaction solution was decanted from the excess dimethylamine hydrochloride solids, rinsing with dichloromethane. The dichloromethane and xylenes were then removed under reduced pressure. The crude brown oil was taken up in CH2Cl2 and washed with water. The dimethylamine hydrochloride solids were taken up in 1:1 CH2Cl2/water. After removal of the organics, the aqueous fraction was extracted three times with CH2Cl2. The combined organics were dried over MgSO4 and concentrated. Purification by flash chromatography (SiO2, gradient eluent: 5% CH2Cl2/hexanes to 10% CH2Cl2/hexanes to 15% CH2Cl2/hexanes) afforded pure 160 as a yellow solid (79% yield).

1. customThe title compound was prepared by the method of Dauzonne, D
2. customSynthesis 1990, 66-70
3. temperaturereflux condenser
4. temperaturethe mixture was heated
5. customthe reaction solution was decanted from the excess dimethylamine hydrochloride solids
6. washrinsing with dichloromethane
7. customThe dichloromethane and xylenes were then removed under reduced pressure
8. washwashed with water
9. customAfter removal of the organics, the aqueous fraction
10. extractionwas extracted three times with CH2Cl2
11. dry with materialThe combined organics were dried over MgSO4
12. concentrationconcentrated
13. customPurification by flash chromatography (SiO2, gradient eluent: 5% CH2Cl2/hexanes to 10% CH2Cl2/hexanes to 15% CH2Cl2/hexanes)