تفاعل #66604

معادلة التفاعل

iodomethane

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

Sodium hydride

ethyl formate

→

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

المردود 48.2%

المذيبات

ظروف التفاعل

المعالجة

1. 1
   أخرىevaporated under a stream of nitrogen
2. 2
   workup.ADDITION10 mL THF was added
3. 3
   workup.ADDITIONwas added in portions
4. 4
   درجة الحرارةAfter 4.5 hours the mixture was cooled
5. 5
   أخرىAfter 16 hours the solution was quenched with H2O
6. 6
   تركيزconcentrated in vacuo
7. 7
   استخلاصextracted with ethyl acetate
8. 8
   غسيلwashed with H2O
9. 9
   غسيلwashed with brine
10. 10
    تجفيفThe combined organic layers were dried over Na2SO4
11. 11
    ترشيحfiltered
12. 12
    تركيزconcentrated in vacuo
13. 13
    أخرىPurification via flash chromatography (9:1 hexane/ethyl acetate)

الإجراء التجريبي

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.

المصدر