Pyridine → (1S)-4-Oxocyclopent-2-en-1-yl benzoate

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Reaction Steps

38 milligrams of the (S)-trans-3-benzoyloxy-5-hydroxycyclopent-1-ene obtained by the method of (1), above, was added in 15 milliliters of methylene chloride to a chromic acid-pyridine complex prepared from 100 milligrams of chromic anhydride and 159 milligrams of pyridine, following which the mixture was stirred for 20 minutes at room temperature. The organic layer was then separated, successively washed in a 5% aqueous NaOH solution, 5% aqueous HCl solution and water and dried, after which the solvent was distilled off to obtain 22 milligrams of 4(S)-benzoyloxycyclopent-2-en-1-one having a Δε226 = -14° and exhibiting the same IR, NMR and mass as those of the product obtained in Example 9. The yield was 58%.

Provenance & Evidence