반응 #4970

반응 방정식

4-cyanobenzaldehyde

methoxymethyl-triphenylphosphonium chloride

→

4-(2-methoxyvinyl)benzonitrile

용매

t-butyl methyl ether

t-butyl methyl ether

반응 조건

후처리

1. 1
   workup.ADDITIONis treated at room temperature
2. 2
   workup.STIRRINGstirred for a further 1 hours
3. 3
   기타Thereafter, the reaction mixture is partitioned in diethyl ether/water
4. 4
   추출The aqueous phase is extracted several times with diethyl ether
5. 5
   세척The organic phases are washed with water
6. 6
   건조dried over magnesium sulfate
7. 7
   여과filtered
8. 8
   기타evaporated
9. 9
   기타Chromatographic purification of the resulting crude product on silica gel with petroleum ether and toluene/hexane (vol. 3:1)

실험 절차

A suspension of 37.2 g of methoxymethyl-triphenylphosphonium chloride in 250 ml of t-butyl methyl ether is treated at room temperature while gassing with argon with 13.4 g of potassium t-butylate and stirred for 1 hour. Subsequently, the reaction mixture is treated at about 20° C. with a mixture of 9.49 g of 4-cyanobenzaldehyde and 100 mol of t-butyl methyl ether and stirred for a further 1 hours. Thereafter, the reaction mixture is partitioned in diethyl ether/water. The aqueous phase is extracted several times with diethyl ether. The organic phases are washed with water, dried over magnesium sulfate, filtered and evaporated. Chromatographic purification of the resulting crude product on silica gel with petroleum ether and toluene/hexane (vol. 3:1) gives 4-(2-methoxyvinyl)benzonitrile.

출처