Synthesis of 3-hydroxy-1-methyl-2-(methylthio) pyrrole from methyl isothiocyanate and prop-2-yn-1-ol |
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| Authors: | L. Brandsma N. A. Nedolya B. A. Trofimov |
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| Affiliation: | (1) Department of Preparative Organic Chemistry, Utrecht University, Padualaan 8, 3584 CH Utrecht, The Netherlands;(2) A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033 Irkutsk, Russian Federation |
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| Abstract: | A methylated adduct of lithiated 1-(1-ethoxyethoxy)allene and methyl isothiocyanate undergoes intramolecular cyclization in the presence of CuBr to give 3-(1-ethoxyethoxy)-1-methyl-2-(methylthio)pyrrole. The methanolysis of the latter affords 3-hydroxy-1-methyl-2-(methylthio)pyrrole. Published inIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1645–1647, September, 2000. |
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| Keywords: | prop-2-yn-1-ol ethoxyethene 1-(1-ethoxyethoxy)allene lithiation methyl isothiocyanate 2-(1-ethoxyethoxy)buta-2,3-dienimidothioate cyclization 3-hydroxy-1-methyl-2-(methylthio)pyrrole keto-enol tautomerism |
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