Ethyl 2-oxocyclopentanecarboxylate → 5-(trifluoromethyl)pyridine-2-sulfonic Acid

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Reaction Steps

A mixture of ethyl 2-oxocyclopentanecarboxylate (148 μl, 1 mmol), N-fluoro-5-(trifluoromethyl)pyridinium-2-sulfonate (245 mg, 1 mmol) and 1,2-dichloroethane (2 ml) was heated under reflux in an argon atmosphere for 6 hours. Thereafter, the precipitate was recovered by filtration and washed with methylene chloride to obtain 5-trifluoromethylpyridine-2-sulfonic acid (217 mg). Yield, 96%. Analysis of the filtrate by 19F-NMR revealed that ethyl 1-fluoro-2-oxocyclopentanecarboxylate was produced at a yield of 57%.

Provenance & Evidence