反応 #1463478

反応方程式

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

収率 56.0%

溶媒

ether

反応条件

後処理

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

実験手順

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).

出典