Sodium Hydroxide → 5-(9-Carboxynona-6,8-dienyl)imidazo[1,5-a]pyridine

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Reaction Steps

To a solution of 6 g 5-(9-ethoxycarbonylnona-6,8-dienyl)imidazo[1,5-a]pyridine in 30 ml of methanol is added 6 ml of 1N sodium hydroxide. The reaction is allowed to stir at room temperature for 3 hours. The methanol is evaporated under reduced pressure and the residue diluted with 15 ml water and the solution adjusted to pH 7 with 1N hydrochloric acid. The solution is extracted with 2×150 ml of ethyl acetate. The combined ethyl acetate extracts are dried over magnesium sulfate, filtered and the solvent evaporated under reduced pressure to yield 5-(9-carboxynona-6,8-dienyl)imidazo[1,5-a]pyridine melting at 120°-122°.

Provenance & Evidence