Reacción #1463484

Ecuación de reacción

tetrahydrofuran

2-(4-(4-cyanophenyl)cyclohexyl)acetaldehyde

Tetrahydrofuran

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

potassium t-butoxide

→

1-(4-(1,3-dioxan-2-yl)-2-butenyl)-4-(4-cyanophenyl)cyclohexane

Rendimiento 50.0%

Disolventes

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroreached 10° C
2. 2
   Otroup to room temperature
3. 3
   Otrofor one hour
4. 4
   workup.STIRRINGstirring for one hour
5. 5
   workup.STIRRINGfurther stirring the reaction mixture for 5 hours
6. 6
   workup.ADDITIONafter completion of the dropwise addition
7. 7
   Filtraciónfiltering off
8. 8
   Concentraciónconcentrating the filtrate under reduced pressure
9. 9
   Otroisolating
10. 10
    Otropurifying the resulting pale brown oil by means of silica gel column chromatography

Procedimiento

Tetrahydrofuran (100 ml) was added to 2-(1,3-dioxan-2-yl)ethyltriphenylphosphonium bromide (19.2 g, 42 mmols), followed by suspending, stirring under ice cooling till the liquid temperature reached 10° C. The reaction mixture was added potassium t-butoxide (4.7 g, 42 mmols), followed by elevating the temperature up to room temperature under ice cooling for one hour, stirring for one hour, dropwise adding a tetrahydrofuran (20 ml) solution of 2-(4-(4-cyanophenyl)cyclohexyl)acetaldehyde (9.0 g, 40 mmols) over 30 minutes from the dropping funnel, further stirring the reaction mixture for 5 hours after completion of the dropwise addition, adding ether (100 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 white solids (6.8 g, 20 mmols) of 1-(4-(1,3-dioxan-2-yl)-2-butenyl)-4-(4-cyanophenyl)cyclohexane.

Fuente