Reacción #84296

Ecuación de reacción

water

tert-butyl N-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]carbamate

potassium carbonate

2,2,2-trifluoroethyl trifluoromethanesulfonate

→

desired product

Rendimiento 76.4%

tert-butyl N-[2-(3,5-dichloropyridin-2-yl)-2-(2,2,2-trifluoroethoxyimino)ethyl]carbamate

Rendimiento 76.4%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter completion of the reaction
2. 2
   Extracciónextracted with ethyl acetate (100 ml×2)
3. 3
   Lavadowashed with water (50 ml×2)
4. 4
   Secadodried over saturated aqueous sodium chloride
5. 5
   Otroanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
6. 6
   OtroThe resulting residue was purified by silica gel column chromatography

Procedimiento

To 5.0 g of tert-butyl N-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]carbamate in 16.0 ml of N,N-dimethylformamide, 4.3 g of potassium carbonate and 5.4 g of 2,2,2-trifluoroethyl trifluoromethanesulfonate were added, and the mixture was stirred at room temperature for 18 hours. After completion of the reaction, the reaction mixture was mixed with 100 ml of water and extracted with ethyl acetate (100 ml×2), the resulting organic layers were combined, washed with water (50 ml×2) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 0:10 to 3:7) as the eluent to obtain 4.8 g of the desired product as a pale yellow oil.

Fuente