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

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.