Ethyl trans-crotonate → Ethyl 4-methyl-1h-pyrrole-3-carboxylate

HRID 234859

Reaktionsgleichung

Reaktionsgleichung von HRID 234859
[C:1]1([CH3:8])[CH:6]=CC(O)=[CH:3][CH:2]=1.S(=[CH:12][N+:13]#[C-:14])(=O)=O.[CH2:15]([O:17][C:18](=[O:22])/[CH:19]=[CH:20]/[CH3:21])[CH3:16]>>[CH3:3][C:2]1[C:1]([CH3:8])=[CH:6][NH:13][CH:12]=1.[CH2:15]([O:17][C:18]([C:19]1[C:20]([CH3:21])=[CH:14][NH:13][CH:12]=1)=[O:22])[CH3:16]

Komponenten

4

Edukt 2

HCID 429065Ethyl trans-crotonateHCID 86750240p-Toluol sulfonylmethyliso-cyanide

Produkt 2

HCID 235044Ethyl 4-methyl-1h-pyrrole-3-carboxylateHCID 53245843,4-Dimethylpyrrole

Versuchsvorschrift

Based on D. O. Cheng, T. L. Bowman, E. LeGoff, J. Heterocyclic Chem. 13, 1145 (1976), 3,4-dimethylpyrrole was synthesized starting from p-toluol-sulfonylmethyliso-cyanide and crotonic-acid-ethyl-ester. The dimethyl compound was quickly obtained after reduction of the intermediary 3-(ethoxycarbonyl)-4-methylpyrrole, but at only 18% total yield. The material had a melting point of 25°-28° C. H-NMR (CDCl3): 2.04 (s, 6H), 6.50 (d, 2H), 7.33 (s br, 1H).

Quellen und Nachweise

ORD-Eintrag
ord-5f12b5c4b65f4ad3aa4980da30b05451
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05597471

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