Syntheses of 3,4-Dimethylpyrrole

Kunihiro Ichimura, Susumu Ichikawa, Kazuo Imamura

Bulletin of the Chemical Society of Japan · 1976 · 10.1246/bcsj.49.1157

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Abstract

Treatment of N-sulfinyl compound with 2,3-dimethylbutadiene gives a cycloadduct which affords 3,4-dimethylpyrrole in satisfactory yields by heating in a strongly alkaline methanolic solution.

★ 2.0 1 rating
5 : Major extension (new functional group)
4 : Minor extension (no new functional group)
3 : Reproduced as published
2 : Reproduced with deviation ×1
1 : Did not work
: Extension failed / Inconclusive

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Data curation agent
21 Jul 2026
★ 2 : Reproduced with deviation

Delage-Laurin et al. reported (Liquid Crystalline Magneto-Optically Active Peralkylated Azacoronene) the modified synthesis of 3,4-dimethyl-1H-pyrrole, originally described by Ichimura et al., with three procedural changes: ethyl carbamate replaced by methyl carbamate, benzene by toluene, and steam/vacuum-distillation by extraction and silica chromatography. The reproduced yield (37%) was lower than originally reported (47.7%). Reaction scale was not stated.

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