Methyl iodide → 2-Methyl-2-phenyl-cyclopentanone

Participants

Reaction Steps

2-Methyl-2-phenyl-cyclopentanone was prepared using the technique described by Ireland et al., J Org. Chem., 31, 2543 (1966). Potassium tert-butoxide (6.2 g, 55 mmol) was added to a solution of 2-phenylcyclopentanone (8.4 g, 53 mmol) in 100 mL of tert-butanol and the solution was stirred at room temperature for 45 min. Iodomethane (6 mL, 100 mmol) was added and after 2 hours the mixture was diluted with water and extracted twice with ether. The ether extract was washed with water and brine, dried (sodium sulfate) and evaporated. Purification of the residue by flash chromatography (5% ethyl acetate-hexane) afforded 8.3 g of 2-methyl-2-phenyl-cyclopentanone as an oil.

Provenance & Evidence