Collect. Czech. Chem. Commun. 2008, 73, 19-23

Electrochemical Preparation of Alkynedial Tetramethyl Acetals

Jaromír Hlavatý* and Miroslav Polášek

J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, v.v.i., Dolejškova 3, 182 23 Prague 8, Czech Republic


Tetramethyl acetals of alkynedials were prepared by anodic oxidation of corresponding alkyne-1,ω-diols (C4 and C6) in trimethyl orthoformate on glassy carbone anode in 80% yield. 1,1,4,4-Tetramethoxybut-2-yne (2a) can be prepared by this one-step procedure from but-2-yne-1,4-diol (1a) instead of a multistep chemical procedure starting from 2,5-dimethoxyfuran. Propargyl alcohol (3) can be similarly anodically oxidized in trimethyl orthoformate giving dimethyl acetal of propynal (4) in 85% yield.

Keywords: Anodic oxidation; Protecting groups; Electrochemistry; Alkynols; Alkynals.

References: 11 live references.