Reacción #1463485

Ecuación de reacción

tetrahydrofuran

tetrahydrofuran

4-(4-propylcyclohexyl)cyclohexanone

potassium t-butoxide

triphenylphosphonium bromide

→

4-(4-propylcyclohexyl)cyclohexane

Rendimiento 56.0%

Disolventes

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroInto a three-necked flask equipped with a dropping funnel
2. 2
   Otroreached 10° C
3. 3
   Otroup to room temperature
4. 4
   Otrofor 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
   Filtraciónfiltering off
9. 9
   Concentraciónconcentrating the filtrate under reduced pressure
10. 10
    Otroisolating
11. 11
    Otropurifying the resulting pale brown oily substance by means of silica gel column chromatography
12. 12
    Otrorecrystallizing from ethanol

Procedimiento

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).

Fuente