6-Methyl-6-phenylfulvene → [1-(Cyclopenta-2,4-dien-1-yl)ethyl]benzene

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Reaction Steps

To a solution of 0.77 mL of dilithio (s)-(-)-2-pyrrolidone-5-carboxylic acid (6 mmol) in 40 mL of ether was added 7.8 mL of n-BuLi (1.6M solution in hexanes, 13 mmol) at 0° C. This solution was stirred for 30 min at room temperature. 6-Methyl-6phenylfulvene, 1.0 g, (6 mmol) was added dropwise at 0° C. and the solution warmed to room temperature. The organic layer was separated and washed with aqueous NaHCO3, H2O and then dried over MgSO4. Removal of solvent gave 1.0 g (99% yield) of 1-cyclopentadienyl-1-phenylethane as a light yellow oil. [α]D =0.0° (CHCl3).

Provenance & Evidence