反应 #1463478

反应方程式

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

收率 56.0%

溶剂

ether

反应条件

后处理

1. 1
   其他Into a three-necked flask equipped with a dropping funnel
2. 2
   其他reached 10° C.
3. 3
   其他up to room temperature
4. 4
   其他for 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
   过滤filtering off
9. 9
   浓缩concentrating the flitrate under reduced pressure
10. 10
    其他isolating
11. 11
    其他purifying the resulting pale brown oil by means of silica gel column chromatography

实验过程

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).

来源