Réaction #43976

Équation de réaction

water

toluene

2-(2,3,4,5-tetramethylcyclopentadienyl)benzaldehyde

phenyllithium

→

{2-(2,3,4,5-tetramethylcyclopentadienyl)phenyl}phenylmethylalcohol

Rendement 87.0%

Solvants

tetrahydrofuran

cyclohexane

ether

Conditions de réaction

Traitement

1. 1
   Autreto separate an organic layer
2. 2
   SéchageThe organic layer was dried over sodium sulfate
3. 3
   workup.DISTILLATIONdistilled
4. 4
   Autreto remove the solvent
5. 5
   Autrepurified by a silica gel column (hexane/ethyl acetate=9/1)

Mode opératoire

To a solution of 2-(2,3,4,5-tetramethylcyclopentadienyl)benzaldehyde (2.0 g, 8.80 mmol) in tetrahydrofuran (34.0 mL) was added dropwise a 1.05 M solution of phenyllithium in cyclohexane and ether (17.7 mL) at −78° C. The temperature of the mixture was raised to room temperature and the mixture was stirred for 4 hrs. To the reaction mixture solution were added deionized water (20.0 mL) and toluene (20.0 mL) to separate an organic layer and an aqueous layer. The organic layer was dried over sodium sulfate, then distilled to remove the solvent, and purified by a silica gel column (hexane/ethyl acetate=9/1) to give {2-(2,3,4,5-tetramethylcyclopentadienyl)phenyl}phenylmethylalcohol (2.83 g, yield 87.0%) as a pale yellow oily substance.

Source