Please use this identifier to cite or link to this item: http://hdl.handle.net/1822/44404

TitleSynthesis of 1-propyl-2-(thiophen-2-yl)-1H-pyrrole
Author(s)Raposo, M. Manuela M.
Issue dateDec-2016
PublisherRoyal Society of Chemistry
Abstract(s)The aim of this work is the synthesis of a thienylpyrrole derivative involving several synthetic transformations, namely: i) synthesis of a secondary gama-ketoamide by direct amidation of the 4-oxo-(2'-thienyl) butanoic acid in the presence of DCC/BtOH coupling reagents; ii) thionation of carbonyl groups using Lawesson´s reagent followed by cyclization of the 4-thioxo derivative yielding the thienylpyrrole heterocyclic system. The students will use several different experimental techniques such as heating at reflux, liquid-liquid extraction, gravity filtration, vacuum filtration, recrystallization, thin layer chromatography (TLC) and column chromatography. The determination of the structure of all synthesized compounds will be also performed through 1H NMR, 13 NMR, IR and UV spectroscopic techniques. The duration of the experiment will be 4 sessions: session 1: preparation of 4-oxo-N-propyl-4-(thiophen-2-yl)butanamide; session 2: purification of of 4-oxo-N-propyl-4-(thiophen-2-yl)butanamide by crystallization, session 3: preparation of 1-propyl-2-(thiophen-2-yl)-1H-pyrrole and session 4: purification of 1-propyl-2-(thiophen-2-yl)-1H-pyrrole using column chromatography on silica gel. The difficulty level of this experiment is medium and the level of study is advanced.
TypeBook part
URIhttp://hdl.handle.net/1822/44404
ISBN978-18-49739-63-4
Publisher versionhttp://pubs.rsc.org/en/content/ebook/978-1-84973-963-4#!divbookcontent
AccessRestricted access (Author)
Appears in Collections:CDQuim - Livros e Capítulos de Livros / Books and Book Chapters

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