반응 #1463485

반응 방정식

tetrahydrofuran

tetrahydrofuran

4-(4-propylcyclohexyl)cyclohexanone

potassium t-butoxide

triphenylphosphonium bromide

→

4-(4-propylcyclohexyl)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 for one hour
6. 6
   workup.STIRRINGfurther stirring the reaction mixture for 5 hours
7. 7
   workup.ADDITIONafter completion of the dropwise addition
8. 8
   여과filtering off
9. 9
   농축concentrating the filtrate under reduced pressure
10. 10
    기타isolating
11. 11
    기타purifying the resulting pale brown oily substance by means of silica gel column chromatography
12. 12
    기타recrystallizing from ethanol

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)ethyl)triphenylphosphonium bromide (12.3 g, 27 mmols), followed by adding tetrahydrofuran (50 ml), suspending, stirring under ice cooling till the liquid temperature reached 10° C. The reaction mixture is added potassium t-butoxide (3.0 g, 27 mmols), followed by elevating the temperature up to room temperature under ice cooling for one hour, stirring for one hour, dropwise adding a tetrahydrofuran (10 ml) solution of 4-(4-propylcyclohexyl)cyclohexanone (15.6 g, 25 mmols) over 30 minutes from the dropping funnel, further stirring the reaction mixture for 5 hours after completion of the dropwise addition, adding ether (50 ml), allowing to stand for one hour, filtering off deposited insoluble substance, concentrating the filtrate under reduced pressure, isolating and purifying the resulting pale brown oily substance by means of silica gel column chromatography and recrystallizing from ethanol, to obtain 1-(2-(1,3-dioxin)-2-yl)ethylidene)-4-(4-propylcyclohexyl)cyclohexane (4.5 g, 14 mmols).

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