تفاعل #69290

معادلة التفاعل

potassium tert-butoxide

diethyl cyanomethylphosphonate

1-formylcyclopropanecarbonitrile

→

product

المردود 19.2%

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

المردود 19.2%

المذيبات

THF

THF

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe cold bath was removed
2. 2
   أخرىwas then recooled to 0° C.
3. 3
   أخرىThe cold bath was removed
4. 4
   workup.ADDITIONThe mixture was then diluted with ether and water
5. 5
   أخرىthe ether solution was separated
6. 6
   غسيلwashed with brine
7. 7
   تجفيفdried over sodium sulfate
8. 8
   ترشيحfiltered
9. 9
   أخرىthe solvent was removed in vacuo
10. 10
    غسيلFlash column chromatography (eluting with a gradient from 0-60% ethyl ether in hexanes)

الإجراء التجريبي

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%).

المصدر