Reacción #950558

Ecuación de reacción

t-BuOK

(2-(1,3-dioxan-2-yl)ethyl)triphenylphosphonium bromide

trans-4-(trans-4-(4-cyanophenyl)cyclohexyl)cyclohexanecarbaldehyde

→

4-(trans-4-(trans-4-(3-(1,3-dioxan-2-yl)propenyl)cyclohexyl)cyclohexyl)benzonitrile

Rendimiento 89.3%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONdropwise adding to the mixture
2. 2
   Otroat -20° C.
3. 3
   workup.STIRRINGlower, stirring the mixture at the same temperature for 2 hours
4. 4
   workup.ADDITIONtreating the reaction product in the same manner as in Example 2
5. 5
   Extracciónexcept that the quantity of ethyl acetate used for extraction

Procedimiento

A mixture of (2-(1,3-dioxan-2-yl)ethyl)triphenylphosphonium bromide (25.0 g, 54.7 millimols) with THF (150 ml) was cooled down to -20° C., followed by adding t-BuOK (6.1 g, 54.7 millimols) to the mixture, stirring for 30 minutes, dropwise adding to the mixture, a THF (80 ml) solution of trans-4-(trans-4-(4-cyanophenyl)cyclohexyl)cyclohexanecarbaldehyde (14.4 g, 49.8 millimols) so as to keep the temperature at -20° C. or lower, stirring the mixture at the same temperature for 2 hours, and treating the reaction product in the same manner as in Example 2, except that the quantity of ethyl acetate used for extraction was made 400 ml, to obtain raw 4-(trans-4-(trans-4-(3-(1,3-dioxan-2-yl)propenyl)cyclohexyl)cyclohexyl)benzonitrile (17.5 g).

Fuente