反应 #2314290

反应方程式

cyclohexanal

4-Pentylcyclohexanal

[3-(4-[2-Tetrahydropyranyloxy]phenyl)propyl]triphenylphosphonium bromide

water

butyllithium

→

(4-(trans-4-Pentylcyclohexyl)-3-butenyl]phenol

溶剂

tert-butyl methyl ether

tert-butyl methyl ether

反应条件

后处理

1. 1
   workup.STIRRINGThe reaction is stirred a further 30 minutes
2. 2
   萃取extracted with ether
3. 3
   洗涤The combined organic layers are washed with brine
4. 4
   干燥dried over sodium sulfate
5. 5
   其他The solvent is removed in vacuo
6. 6
   其他chromatographed

实验过程

To a solution of [3-(4-[2-Tetrahydropyranyloxy]phenyl)propyl]triphenylphosphonium bromide 3D (R=pentyl) (1.68 g) in tert-butyl methyl ether at room temperature is added, dropwise, a 2.6 M solution of butyllithium (1.25 mL). The orange reaction mixture is stirred for 30 minutes, then a solution of cyclohexanal 3F (R=pentyl) (0.558 g) in tert-butyl methyl ether (3 mL) is added dropwise. The reaction is stirred a further 30 minutes, then poured into water and extracted with ether. The combined organic layers are washed with brine, then dried over sodium sulfate. The solvent is removed in vacuo and the residual material is flash chromatographed using 10% ethyl acetate in hexanes as the eluent.

来源