Hydrochloric Acid → Ethyl 3,4-diethyl-1H-pyrrole-2-carboxylate

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Reaction Steps

After 4-acetoxy-3-nitrohexane (11.34 g, 60 mmol) had been added to a reaction vessel, the vessel was replaced with nitrogen, and dry-THF (150 ml) and ethyl isocyanoacetate (7.28 ml, 66 mmol) were added. Then, DBU (20.76 ml, 144 mmol) was slowly dropped while the vessel was cooled in an ice bath, and the whole was stirred at room temperature for 12 hours. After the completion of the reaction, 1 N hydrochloric acid was added, the whole was extracted with chloroform, and the extract was washed with water and a saturated salt solution. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. After that, the concentrated product was purified by means of silica gel column chromatography to yield ethyl 3,4-diethylpyrrole-2-carboxylate (10.97 g, 94% yield).

Provenance & Evidence