Reaktion #1463482

Reaktionsgleichung

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

tetrahydrofuran

tetrahydrofuran

(4-(4-propylphenyl)phenyl)cyclohexanone

potassium t-butoxide

→

4-(4-propylphenyl)phenylcyclohexane

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a three-necked flask equipped with a dropping funnel
2. 2
   Sonstigereached 10° C
3. 3
   SonstigeThe resulting reaction mixture
4. 4
   Sonstigeup to room temperature
5. 5
   Sonstigefor one hour
6. 6
   workup.STIRRINGstirring for one hour
7. 7
   workup.STIRRINGfurther stirring
8. 8
   Sonstigethe reaction liquid for 5 hours
9. 9
   workup.ADDITIONafter completion of the dropwise addition
10. 10
    Filtrationfiltering off
11. 11
    Einengenconcentrating the filtrate under reduced pressure
12. 12
    Sonstigeisolating
13. 13
    Sonstigepurifying the resulting pale brown oil by means of silica gel column chromatography

Vorschrift

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 temperautre reached 10° C. The resulting reaction mixture is added potassium 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 (100 ml) 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 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-(4-propylphenyl)phenylcyclohexane.

Quelle