反応 #1463484

反応方程式

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

収率 50.0%

溶媒

ether

反応条件

後処理

1. 1
   その他reached 10° C
2. 2
   その他up to room temperature
3. 3
   その他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
   ろ過filtering off
8. 8
   濃縮concentrating the filtrate under reduced pressure
9. 9
   その他isolating
10. 10
    その他purifying the resulting pale brown oil by means of silica gel column chromatography

実験手順

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.

出典