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Paper | Regular issue | Vol 36, No. 11, 1993, pp.2541-2547
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6479
Synthesis of 2,3-Dialkoxy-1H-pyrrole via Reduction of Dioxopyrroline with Sodium Hydrosulfite

Takehiro Sano,* Masaharu Seki, Jun Toda, and Yoshisuke Tsuda

*Showa College of Pharmaceutical Sciences, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan


Reductive of 1H-pyrrole-2,3-dione (3 and 7) with sodium hydrosulfite took place selectively in a 1,4-manner. Methylation of the product with diazomethane gave 1,5-dihydro-3-methoxy-2H-pyrrol-2-one (5 and 8) in good yield. Treatment of the methyl ether (5 or 8) with triethyloxonium tetrafluoroborate caused ethylation of the lactam carbonyl with concomitant deprotonation to give 2,3-dialkoxy-1H-pyrrole (9). This conversion provides a simple synthetic method of 2,3-dialkoxypyrroles.