5-[5-Ethoxycarbonyl-5-(phenylsulfinyl)pentyl]-imidazo[1,5-a]pyridine → 5-(5-Ethoxycarbonylpent-4-enyl)-imidazo[1,5-a]pyridine

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Reaction Steps

A solution of 3 g of 5-[5-ethoxycarbonyl-5-(phenylsulfinyl)pentyl]-imidazo[1,5-a]pyridine in 50 ml xylene is heated at reflux temperature for 30 minutes under an atmosphere of nitrogen. The xylene is then removed by distillation under reduced pressure, the residue is dissolved in 15 ml of diethyl ether and purified by column chromatography on silica gel. The product is eluted using a 2:1 mixture of diethyl ether and ethyl acetate as eluent. Evaporation of the solvent yields 5-(5-ethoxycarbonylpent-4-enyl)-imidazo[1,5-a]pyridine as an oil; NMR (CDC13) 1.29 (t,3H), 4.25 (q,2H), 5.88 (d, 1H).

Provenance & Evidence