Water → [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. The solvent was removed under vacuum and 25 mL of hexane added. 6-Methyl-6-phenylfulvene, 1.06 (6 mmol) in 5 mL of hexane was added dropwise at -78° C. The resulting yellow solution was stirred for 7 h at -78° C. Water, 25 mL, was added dropwise at -78° 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 0.8 g (79% yield) of 1-cyclopentadienyl-1-phenylethane as a light yellow oil. [α]D =2.0 ° (CHCl3), 5.8% ee.

Provenance & Evidence