Pyrrole → HCID 19994527, compound

Participants

Reaction Steps

To a cold solution (-5° C. to 0° C.) of sodium hydride in anhydrous dimethylformamide (11.8 g, 245.9 mmol), pyrrole (15.0 g, 223.6 mmol) in dry dimethylformamide was slowly added while stirring vigorously. The reaction was completed, and the temperature raised to room temperature. After hydrogen is fully evolved, iodoacetaldehyde diethyl acetal was added (65.5 g, 268.1 mmol) to the reaction mixture. The reaction mixture was allowed to reflux for 5 hours or until there was no further advance of the reaction. The reaction mixture was cooled to room temperature, poured onto 50 mL of water, extracted with ether, dried over MgSO4, and concentrated. The product was purified by column chromatography [silica gel, hexane] to give the title compound, 1-(2,2-diethoxyethyl)pyrrole, (95%), ms 183 (M+).

Provenance & Evidence