The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Decarboxylation and formylation of certain pyrrole derivatives》. Authors are Chu, Edith Ju-Hwa; Chu, T. C..The article about the compound:Ethyl 3,5-Dimethyl-2-pyrrolecarboxylatecas:2199-44-2,SMILESS:O=C(C1=C(C)C=C(C)N1)OCC).Recommanded Product: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. Through the article, more information about this compound (cas:2199-44-2) is conveyed.
H2NCH2CH2OH (I) is used as decarboxylation agent for substituted carboxypyrroles. Adding 28.5 g. AcCH2CO2Et to Et α-nitroso-α-benzoylacetate (from 38.5 g. BzCH2CO2Et), then adding gradually 28.5 g. Zn dust with gentle boiling, refluxing the mixture 2 hrs., and pouring it into H2O give 63% 2-methyl-4-phenyl-3,5-dicarbethoxypyrrole, colorless prisms, m. 124-5°. 2,4-Dimethyl-3-carboxy-5-carbethoxypyrrole (II), 85%, fine prisms, m. 272° (decomposition), and 2-methyl-4-phenyl-3-carboxy-5-carbethoxypyrrole (III), 78%, platelets, m. 220° (decomposition) are prepared by partial saponification of the corresponding diesters. Refluxing 21.1 g. II and 12.2 g. I 1 hr. and pouring the mixture into H2O give 90% 2,4-dimethyl-5-carbethoxypyrrole (IV), prisms, m. 124.5-5°; similarly, III gives 84% 2-methyl-4-phenyl-5-carbethoxypyrrole, needles, m. 134.5-5°. Gradually adding 15.4 g. POCl3 to 13.4 g. IV and 7.3 g. HCONMe2, refluxing the mixture 2 hrs., pouring it into H2O, and neutralizing it with NaOAc give 95% 2,4-dimethyl-3-formyl-5-carbethoxypyrrole, needles, m. 145-5.5° (oxime, m. 199-200°; semicarbazone, decompose at about 275°). 2-Methyl-4-phenyl-3-formyl-5-carbethoxypyrrole, prepared similarly in 97% yield, prisms, m. 144.5-5° (oxime, 96%, plates, m. 210-11°; semicarbazone, needles, decompose at about 280° with sublimation).
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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com