2-Cyclopenten-1-one → 1-Butylcyclopentanol

Participants

Reaction Steps

nBuLi (1.00 mL; 1.50 mmol; 1.00 equiv) was added to a solution of cyclopentenone (84 mg; 1.0 mmol) in the presence of LaCl3.2LiCl (0.33 M; 3.03 mL, 1.00 mmol, 1.00 equiv) at 0° C. After 2 min, sat. aq. NH4Cl (2 mL) and water (2 mL) was added and the aqueous layer was extracted with ether (4×10 mL). The combined extracts were dried (Na2SO4). Careful evaporation under reduced pressure afforded analytically clean 1-butylcyclopentanol (8) as colorless oil (139 mg, 98%). The analytical data were found to be in accordance with the literature data.

Provenance & Evidence