반응 #2486782

반응 방정식

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

tetrahydrofuran

tetrahydrofuran

(4-(4-propylphenyl)phenyl)cyclohexanone

t-butoxide

→

4-(4-propylphenyl)-phenylcyclohexane

용매

ether

반응 조건

후처리

1. 1
   기타Into a three-necked flask equipped with a dropping funnel
2. 2
   기타reached 10° C
3. 3
   기타The resulting reaction mixture
4. 4
   기타up to room temperature
5. 5
   기타for one hour
6. 6
   workup.STIRRINGstirring for one hour
7. 7
   workup.STIRRINGfurther stirring
8. 8
   기타the reaction liquid for 5 hours
9. 9
   workup.ADDITIONafter completion of the dropwise addition
10. 10
    여과filtering off
11. 11
    농축concentrating the filtrate
12. 12
    기타isolating
13. 13
    기타purifying the resulting pale brown oil by means of silica gel column chromatography

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)ethyltriphenylphosphonium bromide (22.9 g, 50 mmols), followed by adding tetrahydrofuran (100 ml), suspending, stirring the suspension under ice cooling till the liquid temperature reached 10° C. The resulting reaction mixture is added pottasium t-butoxide (5.6 g, 50 mmols), followed by elevating the temperature up to room temperature under ice cooling for one hour, stirring for one hour, dropwise adding a tetrahydrofuran (100ml) solution of (4-(4-propylphenyl)phenyl)cyclohexanone (14.0 g, 48 mmols) over 30 minutes from the dropping funnel, further stirring the reaction liquid for 5 hours after completion of the dropwise addition, adding ether (200 ml), allowing to stand for one hour, filtering off deposited insoluble substance, concentrating the filtrate under reduce pressure and isolating and purifying the resulting pale brown oil by means of silica gel column chromatography, to obtain 1-(2-(2,3-dioxan-2-yl)ethylidene)-4-(4-(4-propylphenyl)-phenylcyclohexane.

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