Reacción #66615

Ecuación de reacción

NaH

iodomethane

(5-chloro-2-isopropyl-4-methoxy-phenoxy)-acetonitrile

ethyl formate

NaH

→

2-(5-chloro-2-isopropyl-4-methoxy-phenoxy)-3-methoxy-acrylonitrile

Rendimiento 84.0%

Disolventes

1,2-dimethoxy ethane

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe mixture was concentrated in vacuo, 1N HCl
2. 2
   workup.ADDITIONwas added
3. 3
   Extracciónthe mixture was extracted with ethyl acetate
4. 4
   LavadoThe combined organic layers were washed with brine
5. 5
   Secadodried over Na2SO4
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   OtroPurification via flash chromatography (85:15 hexane/ethyl acetate)

Procedimiento

To a solution of (5-chloro-2-isopropyl-4-methoxy-phenoxy)-acetonitrile (1.44 g, 6.0 mmol) and ethyl formate (2.2 g, 29.2 mmol) in 7 mL 1,2-dimethoxy ethane at 5° C. was added 95% NaH (0.15 g, 6.0 mmol) in one portion. The mixture was warmed to room temperature. After 1 hour 95% NaH (0.15 g, 6.0 mmol) was added in one portion. After 1 hour 10 mL iodomethane was added and the mixture was allowed to stir for 16 hour. The mixture was concentrated in vacuo, 1N HCl was added and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification via flash chromatography (85:15 hexane/ethyl acetate) afforded 2-(5-chloro-2-isopropyl-4-methoxy-phenoxy)-3-methoxy-acrylonitrile (1.41 g, 84%) as a white solid.

Fuente