반응 #2314290

반응 방정식

cyclohexanal

4-Pentylcyclohexanal

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

water

butyllithium

→

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

용매

tert-butyl methyl ether

tert-butyl methyl ether

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction is stirred a further 30 minutes
2. 2
   추출extracted with ether
3. 3
   세척The combined organic layers are washed with brine
4. 4
   건조dried over sodium sulfate
5. 5
   기타The solvent is removed in vacuo
6. 6
   기타chromatographed

실험 절차

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.

출처