반응 #66604

반응 방정식

iodomethane

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

Sodium hydride

ethyl formate

→

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

수율 48.2%

용매

반응 조건

후처리

1. 1
   기타evaporated under a stream of nitrogen
2. 2
   workup.ADDITION10 mL THF was added
3. 3
   workup.ADDITIONwas added in portions
4. 4
   온도After 4.5 hours the mixture was cooled
5. 5
   기타After 16 hours the solution was quenched with H2O
6. 6
   농축concentrated in vacuo
7. 7
   추출extracted with ethyl acetate
8. 8
   세척washed with H2O
9. 9
   세척washed with brine
10. 10
    건조The combined organic layers were dried over Na2SO4
11. 11
    여과filtered
12. 12
    농축concentrated in vacuo
13. 13
    기타Purification via flash chromatography (9:1 hexane/ethyl acetate)

실험 절차

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.

출처