From 3,3,4,4-Tetraethoxybut-1-yne to furan derivatives

Livi, Francesco (2012) From 3,3,4,4-Tetraethoxybut-1-yne to furan derivatives. [Laurea magistrale], Università di Bologna, Corso di Studio in Chimica industriale [LM-DM270]
Documenti full-text disponibili:
Documento PDF
Download (2MB) | Anteprima


The starting material for this project was the highly functionalized compound 3,3,4,4- tetraethoxybut-1-yne (TEB) and it can be prepared from ethyl vinyl ether by a 4-steps synthesis. The third and the fourth step in TEB synthesis were sensitive to reaction conditions, so it was developed a strategy to try to optimize the third step and obtain TEB with higher yields. An approach, which tries to optimize also the fourth step, will be developed in further works. Several γ-hydroxy-α,β-unsaturated acetylenic ketones can be prepared from 3,3,4,4- tetraethoxybut-1-yne. TEB and γ-hydroxy-α,β-unsaturated acetylenic ketones have been previously synthesized in good yields using various reaction routes. In this work will be shown the synthesis of 1,1-diethoxy-5-hydroxyhex-3-yn-2-one, 1,1-diethoxy-5-hydroxyundec-3-yn-2-one and 1,1-diethoxy-5-hydroxydodec-3-yn-2-one, which will react with ethyl acetoacetate to give, respectively, ethyl 4-(3,3-diethoxy-2-oxopropyl)-2,5-dimethylfuran-3-carboxylate, ethyl 4-(3,3-diethoxy-2-oxopropyl)-5-hexyl-2-methylfuran-3-carboxylate and ethyl 4-(3,3-diethoxy-2-oxopropyl)- 5-heptyl-2-methylfuran-3-carboxylate furan derivatives. This thesis project was carried out during the year 2011, at the Department of Chemistry of the University of Bergen.

Tipologia del documento
Tesi di laurea (Laurea magistrale)
Autore della tesi
Livi, Francesco
Relatore della tesi
Correlatore della tesi
Corso di studio
Ordinamento Cds
Parole chiave
furan derivatives, TEB, modified carbohydrate analogues, Michael addition, cyclopropanation
Data di discussione della Tesi
Marzo 2012

Altri metadati

Statistica sui download

Gestione del documento: Visualizza il documento