Water → {2-(2,3,4,5-Tetramethylcyclopentadienyl)phenyl}phenylmethylalcohol

Participants

Reaction Steps

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. 1H-NMR (CDCl3): δ 7.77-6.91 (4H), 6.45-5.55 (2H), 3.21-2.25 (1H), 1.88-1.45 (9H), 1.16-0.82 (3H);

Provenance & Evidence