反応 #2314290

反応方程式

cyclohexanal

4-Pentylcyclohexanal

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

water

butyllithium

→

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

溶媒

tert-butyl methyl ether

tert-butyl methyl ether

反応条件

後処理

1. 1
   workup.STIRRINGThe reaction is stirred a further 30 minutes
2. 2
   抽出extracted with ether
3. 3
   洗浄The combined organic layers are washed with brine
4. 4
   乾燥dried over sodium sulfate
5. 5
   その他The solvent is removed in vacuo
6. 6
   その他chromatographed

実験手順

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.

出典