Reacción #66604

Ecuación de reacción

iodomethane

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

Sodium hydride

ethyl formate

→

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

Rendimiento 48.2%

Disolventes

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroevaporated under a stream of nitrogen
2. 2
   workup.ADDITION10 mL THF was added
3. 3
   workup.ADDITIONwas added in portions
4. 4
   TemperaturaAfter 4.5 hours the mixture was cooled
5. 5
   OtroAfter 16 hours the solution was quenched with H2O
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   Extracciónextracted with ethyl acetate
8. 8
   Lavadowashed with H2O
9. 9
   Lavadowashed with brine
10. 10
    SecadoThe combined organic layers were dried over Na2SO4
11. 11
    Filtraciónfiltered
12. 12
    Concentraciónconcentrated in vacuo
13. 13
    OtroPurification via flash chromatography (9:1 hexane/ethyl acetate)

Procedimiento

Sodium hydride (0.122 g, 5.0 mmol, 60% w/w) was washed with dry hexanes and evaporated under a stream of nitrogen. 10 mL THF was added and the mixture was cooled to 0° C. (5-Bromo-2-isopropyl-4-methoxy-phenoxy)-acetonitrile (0.577 g, 2.03 mmol) was added in portions. After 30 min ethyl formate (4.9 mL, 60.9 mmol) was added and the solution was warmed to 80° C. After 4.5 hours the mixture was cooled and 5.0 mL iodomethane was added in one portion. After 16 hours the solution was quenched with H2O, concentrated in vacuo, extracted with ethyl acetate, washed with H2O and then washed with brine. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification via flash chromatography (9:1 hexane/ethyl acetate) afforded 2-(5-bromo-2-isopropyl-4-methoxy-phenoxy)-3-methoxy-acrylonitrile (0.319 g, 48%) as a white solid.

Fuente