Hydrochloric Acid → ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate

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Reaction Conditions

Reaction Steps

2,4-Diethoxycarbonyl-3,5-dimethylpyrrole (2.0 g) was dissolved in ethanol (20 ml), and a 1 N sodium hydroxide solution (20 ml) was added and stirred overnight at 80° C. After cooling to room temperature, the reaction mixture was neutralized with a hydrochloric acid solution. The precipitate was collected by filtration, and dried in vacuo. The obtained solid was dissolved in trifluoroacetic acid (20 ml), and stirred for 1 hour at 40° C. While cooling with ice, triethyl orthoformate (2.5 ml) was slowly added dropwise to the reaction mixture. The mixture was allowed to room temperature, and then stirred for 2 hours. The resultant was concentrated at reduced pressure. The residue was added to a saturated sodium hydrogencarbonate and stirred, and then the precipitate was collected by filtration. The obtained solid was purified using medium pressure silica gel flash column chromatography (hexane:ethyl acetate=5:1 to 1:1), and dried in vacuo to afford 5-formyl-2,4-dimethyl-pyrrole-3-carboxylic acid ethyl ester (1.21 g, 74%) as a light yellow solid.

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