R. Brisbois, William G. Batterman, S. Kragerud
Jul 1, 1997
Citations
0
Influential Citations
2
Citations
Journal
Journal of Chemical Education
Abstract
A procedure for the preparation and purification of tetrahydro-2-(2-propynyloxy)-2H-pyran is reported for use as an introductory organic laboratory exercise. Synthesis of the target compound illustrates Markownikov Addition and formation of a THP-ether protecting group, produces an acetal functional group, and models a recently developed resin used in combinatorial chemistry. Purification of the target compound via flash column chromatography exposes students to a central technique of modern synthetic methodology. Analysis of the target compound via 1H NMR introduces non-first order coupling (i.e. AB quartet) and long range (i.e. 4-bond) coupling.