2-(3-Methoxyphenyl)-cyclopentanol → 2-(3-Methoxyphenyl)cyclopentan-1-one

Participants

Reaction Steps

To a solution of 2-(3-methoxyphenyl)-cyclopentanol (6.4 g, 0.033 mmoles) in 140 ml of methylene chloride, add a mixture of pyridine chlorochromate (14.4 g, 0.066 mmoles), and silica gel (14.4 g). After 1.5 hours, an equivalent amount of oxidizing agent and silica gel is added and the reaction is stirred an additional 3.5 hours. Reduce the solvent in half in vacuo at 35° C. and chromatograph on silica with 3-1 hexanes-ethyl acetate to yield 4.34 g of the titled compound. 1H NMR (CDCl3): 7.25 (m, 1H), 6.81-6.74 (m, 3H), 3.8 (s, 3H), 3.31 (m, 1H), 2.5 (m, 2H), 2.3 (m, 1H), 2.1 (m, 2H), 1.9 (m, 1H).

Provenance & Evidence