Regioselective functionalization of heterocyclic rings: synthesis and reactions of 1-methyl-2-(trimethylsiloxy) pyrrole and 2-(trimethylsiloxy) thiophene

M Fiorenza, G Reginato, A Ricci, M Taddei…

Index: Fiorenza, Mariella; Reginato, Gianna; Ricci, Alfredo; Taddei, Maurizio; Dembech, Pasquale Journal of Organic Chemistry, 1984 , vol. 49, # 3 p. 551 - 553

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Citation Number: 36

Abstract

2a, X= NMe b, X= S 1 detected in the reaction mixture at-78" C but rapidly decomposed at room temperature, probably owing to the presence of diethylamine produced during the reaction. Addition of 2 equiv of trimethylchlorosilane (Me3SiC1) and 1.2 equiv of Me3SiDEA to 2b gave lb in 65% yield, after distillation, as a colorless oil that could be kept indefinitely under an inert atmosphere.