Please use this identifier to cite or link to this item:

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
Publisher version!divbookcontent
AccessRestricted access (Author)
Appears in Collections:CDQuim - Livros e Capítulos de Livros / Books and Book Chapters

Files in This Item:
File Description SizeFormat 
Chapter 225, Experiment 17.8, p 1025-1030 -Synthesis of 1-propyl-2-(thiophen-2-yl)-1H-pyrrole revised.pdf
  Restricted access
221,61 kBAdobe PDFView/Open

Partilhe no FacebookPartilhe no TwitterPartilhe no DeliciousPartilhe no LinkedInPartilhe no DiggAdicionar ao Google BookmarksPartilhe no MySpacePartilhe no Orkut
Exporte no formato BibTex mendeley Exporte no formato Endnote Adicione ao seu ORCID