L-Proline → HCID 11116496, compound

Participants

Reaction Steps

n-BuLi (15 mL, 1.6M in hexanes, 24 mmol) was added dropwise to 1.4 g (12 mmol) of L-proline in 40 mL of ether. The resulting suspension was allowed to stir at room temperature over night. The reaction mixture was cooled to -78° C. and 2.0 g (12 mmol) of 6-methyl-6-phenylfulvene added dropwise. The reaction mixture was stirred at -78° C. for eight hours. The reaction mixture was allowed to warm to room temperature and the organic and aqueous layers were separated. The organic layer was dried over MgSO4 and the solvent removed under vacuum to give 2.05 g (100% yield) of (1-phenylethyl)cyclopentadiene as a yellow oil. The product was found to have a specific rotation of 4°(12% ee) .

Provenance & Evidence