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  Home > JCE Print > Journal of Chemical Education > Issues > 1997  > July  >
In the Laboratory
The Microscale Laboratory
Synthesis of Tetrahydro-2-(2-propynyloxy)-2H-pyran: Illustrating Markownikov Addition, Protecting Groups, and Advance 1H-NMR Phenomena
Ronald G. Brisbois, William G. Batterman, and Scott R. Kragerud
Cover
July 1997
Vol. 74 No. 7
p. 834
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.
More Information
*  Citation
 Brisbois, Ronald G. ; Batterman, William G. ; Kragerud, Scott R. . J. Chem. Educ. 1997 74 834.
*  Keywords
 Organic Chemistry, Laboratory Instruction, Microscale, NMR Spectrometry, Catalysis
*  History
 Created:
Last Updated:		 July 28, 1999
June 23, 2005
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