反应详情

Heat a mixture of 4,4,5,5,5-pentafluoro-3-oxo-pentanenitrile (4.0 g, 21.4 mmol) and p-tolyl-hydrazine (10 g, 64.1 mmol) in ethanol (20 mL) to 95° C. in a sealed tube apparatus for 15 hours. After cooling to room temperature, remove the solvent under reduced pressure to give a yellow solid. Distribute the solid between dichloromethane (250 mL), distilled water (150 mL) and a saturated aq. sodium bicarbonate solution (50 mL). Isolate the aqueous phase and extract with dichloromethane (100 mL). Dry the combined organic phases over sodium sulfate and concentrate to give a dark gold oil. Subject oil to silica gel chromatography eluting with ethyl acetate and hexanes to give a light brown solid (3.24 g, 52% yield). MS(ES+): m/z=292.1 [M+H].

1. temperatureHeat
2. customremove the solvent under reduced pressure
3. customto give a yellow solid
4. distillationdistilled water (150 mL)
5. customIsolate the aqueous phase
6. extractionextract with dichloromethane (100 mL)
7. dry with materialDry the combined organic phases over sodium sulfate
8. concentrationconcentrate
9. customto give a dark gold oil
10. washeluting with ethyl acetate and hexanes