Реакция #73322

Уравнение реакции

potassium tert-butoxide

diethyl cyanomethylphosphonate

1-formylcyclopropanecarbonitrile

→

product

Выход 19.2%

1-[(E)-2-Cyanovinyl]cyclopropanecarbonitrile

Выход 19.2%

Растворители

THF

THF

THF

Условия реакции

Обработка

1. 1
   ДругоеThe cold bath was removed
2. 2
   ТемператураThe solution was then re-cooled to 0° C.
3. 3
   ДругоеThe cold bath was removed
4. 4
   workup.ADDITIONThe mixture was then diluted with ether and water
5. 5
   Другоеthe ether solution was separated
6. 6
   Промывкаwashed with brine
7. 7
   Сушкаdried over sodium sulfate
8. 8
   Фильтрацияfiltered
9. 9
   Другоеthe solvent was removed in vacuo
10. 10
    ПромывкаFlash column chromatography (eluting with a gradient from 0-60% ethyl ether in hexanes)

Методика

To a solution of 1.0 M potassium tert-butoxide in THF (1.12 mL) at 0° C. was added slowly dropwise a solution of diethyl cyanomethylphosphonate (210 mg, 1.2 mmol) in THF (2 mL). The cold bath was removed and the reaction was warmed to ambient temperature. The solution was then re-cooled to 0° C. and a solution of 1-formylcyclopropanecarbonitrile (101 mg, 1.06 mmol) in THF (1.0 mL) was added dropwise. The cold bath was removed and the reaction was stirred for 3 hours at ambient temperature. The mixture was then diluted with ether and water, the ether solution was separated, washed with brine, dried over sodium sulfate, filtered and the solvent was removed in vacuo. Flash column chromatography (eluting with a gradient from 0-60% ethyl ether in hexanes) afforded the product (24 mg, 19%).

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