Reacción #1463478

Ecuación de reacción

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

tetrahydrofuran

tetrahydrofuran

4-(4-cyanophenyl)cyclohexanone

potassium t-butoxide

→

1-(2-(1,3-dioxan-2-yl)ethylidene)-4-(4-cyanophenyl)-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 the mixture for one hour
6. 6
   workup.STIRRINGThe reaction mixture was stirred for 5 hours
7. 7
   workup.ADDITIONafter completion of the dropwise addition
8. 8
   Filtraciónfiltering off
9. 9
   Concentraciónconcentrating the flitrate under reduced pressure
10. 10
    Otroisolating
11. 11
    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 (12.2 g, 27 mmols), followed by adding tetrahydrofuran (200 ml), suspending, stirring the suspension under ice cooling till the liquid temperature reached 10° C., adding to the reaction mixture, potassium t-butoxide (30 g, 27 mmols), elevating the temperaure up to room temperature under ice cooling for one hour, stirring the mixture for one hour, dropwise adding a tetrahydrofuran (50 ml) solution of 4-(4-cyanophenyl)cyclohexanone (5.0 g, 25 mmols) from the dropping funnel over 30 minutes. The reaction mixture was stirred for 5 hours after completion of the dropwise addition, followed by adding ether (100 ml), allowing the mixture to stand, filtering off deposited insoluble substance, concentrating the flitrate 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-cyanophenyl)-cyclohexane (4.1 g, 14 mmols).

Fuente