반응 #43976

반응 방정식

water

toluene

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

phenyllithium

→

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

수율 87.0%

용매

tetrahydrofuran

cyclohexane

ether

반응 조건

후처리

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

실험 절차

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.

출처