反应 #1463484

反应方程式

tetrahydrofuran

2-(4-(4-cyanophenyl)cyclohexyl)acetaldehyde

Tetrahydrofuran

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

potassium t-butoxide

→

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

收率 50.0%

溶剂

ether

反应条件

后处理

1. 1
   其他reached 10° C
2. 2
   其他up to room temperature
3. 3
   其他for one hour
4. 4
   workup.STIRRINGstirring for one hour
5. 5
   workup.STIRRINGfurther stirring the reaction mixture for 5 hours
6. 6
   workup.ADDITIONafter completion of the dropwise addition
7. 7
   过滤filtering off
8. 8
   浓缩concentrating the filtrate under reduced pressure
9. 9
   其他isolating
10. 10
    其他purifying the resulting pale brown oil by means of silica gel column chromatography

实验过程

Tetrahydrofuran (100 ml) was added to 2-(1,3-dioxan-2-yl)ethyltriphenylphosphonium bromide (19.2 g, 42 mmols), followed by suspending, stirring under ice cooling till the liquid temperature reached 10° C. The reaction mixture was added potassium t-butoxide (4.7 g, 42 mmols), followed by elevating the temperature up to room temperature under ice cooling for one hour, stirring for one hour, dropwise adding a tetrahydrofuran (20 ml) solution of 2-(4-(4-cyanophenyl)cyclohexyl)acetaldehyde (9.0 g, 40 mmols) over 30 minutes from the dropping funnel, further stirring the reaction mixture for 5 hours after completion of the dropwise addition, adding ether (100 ml), allowing to stand for one hour, filtering off deposited insoluble substance, concentrating the filtrate under reduced pressure and isolating and purifying the resulting pale brown oil by means of silica gel column chromatography, to obtain white solids (6.8 g, 20 mmols) of 1-(4-(1,3-dioxan-2-yl)-2-butenyl)-4-(4-cyanophenyl)cyclohexane.

来源