Reacción #1062921

Ecuación de reacción

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

tetrahydrofuran

tetrahydrofuran

(4-(4-propylphenyl)phenyl)cyclohexanone

t-butoxide

→

4-(4-propylphenyl)-phenylcyclohexane

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
   OtroThe resulting reaction mixture
4. 4
   Otroup to room temperature
5. 5
   Otrofor one hour
6. 6
   workup.STIRRINGstirring for one hour
7. 7
   workup.STIRRINGfurther stirring
8. 8
   Otrothe reaction liquid for 5 hours
9. 9
   workup.ADDITIONafter completion of the dropwise addition
10. 10
    Filtraciónfiltering off
11. 11
    Concentraciónconcentrating the filtrate under reduced pressure
12. 12
    Otroisolating
13. 13
    Otropurifying the resulting pale brown oil by means of silica gel column chromatography

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)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 (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-dioxane-2-yl)ethylidene)-4-(4-(4-propylphenyl)-phenylcyclohexane.

Fuente