Реакция #43976

Уравнение реакции

water

toluene

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

phenyllithium

→

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

Выход 87.0%

Растворители

tetrahydrofuran

cyclohexane

ether

Условия реакции

Обработка

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

Методика

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.

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