반응 #69290

반응 방정식

potassium tert-butoxide

diethyl cyanomethylphosphonate

1-formylcyclopropanecarbonitrile

→

product

수율 19.2%

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

수율 19.2%

용매

THF

THF

THF

반응 조건

후처리

1. 1
   기타The cold bath was removed
2. 2
   기타was then recooled to 0° C.
3. 3
   기타The cold bath was removed
4. 4
   workup.ADDITIONThe mixture was then diluted with ether and water
5. 5
   기타the ether solution was separated
6. 6
   세척washed with brine
7. 7
   건조dried over sodium sulfate
8. 8
   여과filtered
9. 9
   기타the solvent was removed in vacuo
10. 10
    세척Flash column chromatography (eluting with a gradient from 0-60% ethyl ether in hexanes)

실험 절차

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 recooled 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%).

출처