Reaktion #1696616

Reaktionsgleichung

4-(4-propylcyclohexyl)cyclohexylacetaldehyde

potassium-t-butoxid

triphenylphosphite

4-bromophenethylbromide

4-bromophenethylalcohol

→

4-(4-propylcyclohexyl)cyclohexyl-2Z-butene

Lösungsmittel

THF

xylene

ether

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a flask, were placed
2. 2
   workup.ADDITIONby adding
3. 3
   Temperaturheating under reflex for 10 hours
4. 4
   Sonstigeafter the completion of reaction
5. 5
   Filtrationfiltering off the deposited white crystals of 4-bromo-phenethyltriphenylphosphoniumbromide
6. 6
   workup.STIRRINGstirring the solution at room temperature for 2 hours after the completion
7. 7
   workup.STIRRINGfurther stirring for 5 hours
8. 8
   Sonstigeafter the completion of reaction
9. 9
   Filtrationfiltrating off white solid
10. 10
    Einengenconcentrating the filtrate under reduced pressure
11. 11
    Sonstigepurifying the obtained brown oil by means of silica gel chromatography

Vorschrift

Into a flask, were placed triphenylphosphite (2.6 g, 10 mmol) and 4-bromophenethylbromide (2.6 g, 10 mmol) prepared from 4-bromophenethylalcohol, followed by adding and dissolving xylene (10 ml), heating under reflex for 10 hours after the completion of reaction, filtering off the deposited white crystals of 4-bromo-phenethyltriphenylphosphoniumbromide, and drying the white crystals (5.1 g, 9.5 mmol). The obtained white crystals were dissolved into THF (30 ml), followed by stirring under ice cooling, adding potassium-t-butoxid (1 g, 9 mmol) slowly into the reaction solution, stirring the solution at room temperature for 2 hours after the completion of dropping, adding THF (20 ml) solution of 4-(4-propylcyclohexyl)cyclohexylacetaldehyde (2.2 g, 9 mmol), further stirring for 5 hours, adding ether after the completion of reaction, filtrating off white solid deposited, concentrating the filtrate under reduced pressure, purifying the obtained brown oil by means of silica gel chromatography, to obtain a mixture (2.2 g, 5.3 mmol) of 1-(4-bromophenyl)-4-(4-(4-propylcyclohexyl)cyclohexyl-2Z-butene with its E-isomer.

Quelle