0

Linchpin Construction of Unsymmetrical 1,4-alkynediols

Douglass F Taber, Pierre H Storck

J Org Chem. 2002 Nov 15;67(23):8273-5.

PMID: 12423169

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP811494 Ethyllithium solution Ethyllithium solution 811-49-4 Price
qrcode