Water → HCID 12390807, compound

Participants

Reaction Steps

A solution of dimethyl N-(4-methoxyphenyl)-2,5-dimethylpyrrole-3,4-dicarboxylate (0.04 mol) in dry dichloromethane (50 mL) was added dropwise over a 15-min period to a mechanically stirred mixture of lithium aluminum hydride (3.4 g, 0.08 mol) in anhydrous ether (100 mL) heated under reflux (50°-55° C. bath). The stirred mixture was heated under reflux for 1 h after the addition was complete and then cooled in an ice bath. The excess hydride was carefully decomposed with small additions of wet ether and then with water until the salts were white. The mixture was filtered (medium-porosity sintered-glass funnel) and the inorganic residue was washed with several portions of hot dichloromethane (about 30 mL) until the total filtrate volume was about 400 mL. The filtrate was concentrated in vacuo to a volume of about 125 mL, warmed to boiling, and diluted with slow portionwise addition of petroleum ether (about 100 mL) to yield 91% of N-(4-methoxyphenyl)-2,5-dimethyl-3,4-bis(hydroxymethyl)pyrrole: mp 143°-145° C. (dec).

Provenance & Evidence