反应 #1076759

反应方程式

t-BuOK

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

4-(trans-4-propylcyclohexyl)cyclohexanone

→

2-(4-(trans-4-propylcyclohexyl)cyclohexylidene)-ethyl-1,3-dioxane

溶剂

THF

THF

反应条件

后处理

1. 1
   温度while being maintained at a temperature lower than −30° C
2. 2
   温度the reaction temperature was gradually raised up to room temperature and they
3. 3
   workup.STIRRINGwere stirred for further 5 hours
4. 4
   过滤The reaction mixture was filtered with Celite
5. 5
   workup.DISTILLATIONthe solvent was distilled off under a reduced pressure
6. 6
   workup.ADDITIONthe residue was subjected to silica gel column chromatography (eluent: mixed solvent of toluene/ethyl acetate=9/1)

实验过程

Under nitrogen gas stream, a mixture of 1330 g (2930 mmol) of 2-(1,3-dioxane-2-yl)ethyltriphenylphosphonium bromide with 6.0 l of THF was cooled down to −30° C., and 303 g (2700 mmol) of t-BuOK was added thereto and stirred for 1 hour. To this mixture was added by drops a solution of 500 g (2250 mmol) of 4-(trans-4-propylcyclohexyl)cyclohexanone in 3.0 l of THF while being maintained at a temperature lower than −30° C. After finishing of the adding, the reaction temperature was gradually raised up to room temperature and they were stirred for further 5 hours. The reaction mixture was filtered with Celite, the solvent was distilled off under a reduced pressure, and the residue was subjected to silica gel column chromatography (eluent: mixed solvent of toluene/ethyl acetate=9/1) to obtain 652 g of a crude 2-(2-(4-(trans-4-propylcyclohexyl)cyclohexylidene)-ethyl-1,3-dioxane.

来源