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Linchpin construction of unsymmetrical 1,4-alkynediols
Douglass F Taber1, Pierre H Storck
1Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@Udel.edu
The Journal of Organic Chemistry
|November 9, 2002
Abstract:
A one-pot preparation of unsymmetrical 1,4-alkynediols such as 2a by the coupling of trimethylsilylacetylene and two different aldehydes or ketones is reported. The dilithiated species 5 is generated by the sequential addition of the first aldehyde or ketone 1b to a solution of lithium trimethylsilylacetylide, followed by the addition of methyllithium, which removes the trimethylsilyl protecting group. Addition of the second aldehyde or ketone then leads to the unsymmetrical 1,4-alkynediol 2a.