Reacción #710501

Ecuación de reacción

1-[2-chloro-6-(trifluoromethyl)pyridin-3-yl]-2-nitroethanol

acetic anhydride

→

2-chloro-3-[(E)-2-nitrovinyl]-6-(trifluoromethyl)pyridine

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter completion of reaction
2. 2
   Otrothe reaction mixture was quenched with ice water
3. 3
   Extracciónextracted with dichloromethane (2×200 mL)
4. 4
   LavadoThe combined organic layer was washed with water (200 mL), brine (200 mL)
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   Otrothe solvent was removed under reduced pressure

Procedimiento

To a stirred solution of 1-[2-chloro-6-(trifluoromethyl)pyridin-3-yl]-2-nitroethanol (Int-18) (27 g, 1.0 eq.) in dichloromethane (270 mL) was added 4-dimethylamino pyridine (13.5 g, 1.1 eq.) followed by drop wise addition of acetic anhydride (13.5 g, 1.3 eq) at 0° C. and stirred for 15 min. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mixture was quenched with ice water and extracted with dichloromethane (2×200 mL). The combined organic layer was washed with water (200 mL), brine (200 mL), dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to get crude 2-chloro-3-[(E)-2-nitrovinyl]-6-(trifluoromethyl)pyridine (Int-19) (22.0 g, 87.6%).

Fuente