反应 #1076761

反应方程式

t-BuOK

methoxymethyltriphenylphosphonium chloride

3-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)propanal

→

1-methoxy-4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)butene

收率 57.3%

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
3. 3
   workup.STIRRINGthe mixture was 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

实验过程

Under nitrogen gas stream, a mixture of 405 g (1180 mmol) of methoxymethyltriphenylphosphonium chloride with 4.0 l of THF was cooled down to −30° C., 122 g (1090 mmol) of t-BuOK was added thereto, and they were stirred for 1 hour. To this mixture was added by drops a solution of 240 g (907 mmol) of the crude 3-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)propanal in 2.4 l of THF while being maintained at a temperature lower than −30° C. After finishing of the dropping, the reaction temperature was gradually raised up to room temperature, and the mixture was 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: heptane) to obtain 152 g of a crude 1-methoxy-4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)butene.

来源