Isopropanol → HCID 58070832, compound

Participants

Reaction Steps

A solution of Jones reagent (1.67 M, 60 ml, 100 mmol) is added, dropwise, to a solution of 5-(4-benzyloxy-2,6-dimethylphenyl)-4-hydroxycyclopent-2-enone (30.9 g) in acetone (500 ml) at 0° C., and the resulting solution is stirred at 0° C. for 2 hours. Propan-2-ol (50 ml) is added and the mixture is stirred for a further 2 hours, then brine (200 ml) is added and the reaction mixture is extracted with ethyl acetate (2×250 ml). The organic extracts are combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to give 2-(4-benzyloxy-2,6-dimethylphenyl)cyclopent-4-ene-1,3-dione (18.1 g).

Provenance & Evidence