반응 #1463478

반응 방정식

2-(1,3-dioxan-2-yl)ethyltriphenylphosphonium bromide

tetrahydrofuran

tetrahydrofuran

4-(4-cyanophenyl)cyclohexanone

potassium t-butoxide

→

1-(2-(1,3-dioxan-2-yl)ethylidene)-4-(4-cyanophenyl)-cyclohexane

수율 56.0%

용매

ether

반응 조건

후처리

1. 1
   기타Into a three-necked flask equipped with a dropping funnel
2. 2
   기타reached 10° C.
3. 3
   기타up to room temperature
4. 4
   기타for one hour
5. 5
   workup.STIRRINGstirring the mixture for one hour
6. 6
   workup.STIRRINGThe reaction mixture was stirred for 5 hours
7. 7
   workup.ADDITIONafter completion of the dropwise addition
8. 8
   여과filtering off
9. 9
   농축concentrating the flitrate under reduced pressure
10. 10
    기타isolating
11. 11
    기타purifying the resulting pale brown oil by means of silica gel column chromatography

실험 절차

Into a three-necked flask equipped with a dropping funnel, a three-way cock and a thermometer, was placed 2-(1,3-dioxan-2-yl)ethyltriphenylphosphonium bromide (12.2 g, 27 mmols), followed by adding tetrahydrofuran (200 ml), suspending, stirring the suspension under ice cooling till the liquid temperature reached 10° C., adding to the reaction mixture, potassium t-butoxide (30 g, 27 mmols), elevating the temperaure up to room temperature under ice cooling for one hour, stirring the mixture for one hour, dropwise adding a tetrahydrofuran (50 ml) solution of 4-(4-cyanophenyl)cyclohexanone (5.0 g, 25 mmols) from the dropping funnel over 30 minutes. The reaction mixture was stirred for 5 hours after completion of the dropwise addition, followed by adding ether (100 ml), allowing the mixture to stand, filtering off deposited insoluble substance, concentrating the flitrate under reduced pressure, and isolating and purifying the resulting pale brown oil by means of silica gel column chromatography, to obtain 1-(2-(1,3-dioxan-2-yl)ethylidene)-4-(4-cyanophenyl)-cyclohexane (4.1 g, 14 mmols).

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