2-Phenylethanol → Methyl 7-(2-oxocyclopentyl)heptanoate

Participants

Reaction Steps

A solution of 8.8 g. of 7-(5-oxo-1-cyclopentenyl)-cis-5-heptenoic acid, methyl ester and 6.6 g. of tris-(triphenylphosphine) rhodium (I) chloride in 800 ml. of 1:1 benzene-ethanol is hydrogenated at 25° and atmospheric pressure until 1 equivalent of hydrogen was absorbed. The solvents are evaporated and the resulting residue dissolved in 1:1 ethyl acetate-hexane and flushed through a silica column. The crude product is then rechromatographed on silica with 15% ethyl acetate in hexane to obtain 7.2 g. of the title product as an oil.

Provenance & Evidence