Methanol → 3-(2-Thenoyl)-2-methyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylic acid

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Reaction Steps

A solution of 900 mg. of isopropyl 3-(2-thenoyl)-2-methyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate in 15 ml. of methanol is treated with a solution of 125 g. of potassium carbonate in 10 ml. of water. The reaction mixture is refluxed under nitrogen atmosphere for 3 hours, cooled, and evaporated to dryness. The residue is taken up in 50 ml. of water, cooled to 0° and made acidic with 10% aqueous hydrochloric acid. The resultant mixture is extracted with ethyl acetate (3×50 ml.). The extracts are dried over magnesium sulfate and evaporated to dryness under reduced pressure, to give 3-(2-thenoyl)-2-methyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylic acid (XIIa, R=CH3, M=H, X=S, n=1).

Provenance & Evidence