Reacción #304284

Ecuación de reacción

Potassium t-butoxide

trichloroacetonitrile

→

t-Butyl trichloroacetimidate

Disolventes

diethyl ether

diethyl ether

—

hexanes

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThis solution was added dropwise, over 30 minutes
2. 2
   Temperaturawith heating
3. 3
   Temperaturaat reflux
4. 4
   TemperaturaThe mixture was cooled to room temperature
5. 5
   Otroevaporated under reduced pressure
6. 6
   Otroto yield an oil
7. 7
   Filtración140 mL, and filtered
8. 8
   Otroto remove potassium salts
9. 9
   OtroThe filtrate was evaporated under reduced pressure
10. 10
    workup.DISTILLATIONdistilled
11. 11
    workup.DISTILLATIONThe fraction distilling at 2.4 mm Hg and 40° C.
12. 12
    Otrowas collected

Procedimiento

Potassium t-butoxide (1M in t-butanol), 69 mL (0.069 mole), was dissolved in diethyl ether, 69 mL. This solution was added dropwise, over 30 minutes, to a cold, 0° C., solution of trichloroacetonitrile, 100 g (0.69 mole), in diethyl ether, 69 mL. The mixture was allowed to warm to room temperature over one hour, and was then stirred for an additional hour with heating at reflux. The mixture was cooled to room temperature and evaporated under reduced pressure to yield an oil. The oil was dissolved in hexanes, 140 mL, and filtered to remove potassium salts. The filtrate was evaporated under reduced pressure and the residue was vacuum distilled. The fraction distilling at 2.4 mm Hg and 40° C. was collected. The yield was 105 g, 69% based on trichloroacetonitrile. 1H nmr (300 MHz CDCl3) δ (ppm): 1.58, (s, 9H), 8.21 (br, s, 1H). 13C (75.45 MHz, CDCl3) δ (ppm): 27.23, 83.86, 92.78, 160.33. (Armstrong et al.)

Fuente