Reacción #2314290

Ecuación de reacción

cyclohexanal

4-Pentylcyclohexanal

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

water

butyllithium

→

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

Disolventes

tert-butyl methyl ether

tert-butyl methyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe reaction is stirred a further 30 minutes
2. 2
   Extracciónextracted with ether
3. 3
   LavadoThe combined organic layers are washed with brine
4. 4
   Secadodried over sodium sulfate
5. 5
   OtroThe solvent is removed in vacuo
6. 6
   Otrochromatographed

Procedimiento

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.

Fuente