Synthesis of Tetrahydro-2-(2-propynyloxy)-2H-pyran: Illustrating Markownikov Addition, Protecting Groups, and Advance 1H-NMR Phenomena
Synthesis of Tetrahydro-2-(2-propynyloxy)-2H-pyran: Illustrating Markownikov Addition, Protecting Groups, and Advance 1H-NMR Phenomena
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四氢-2-(2-丙炔氧基)-2H-吡喃的合成：说明马氏加成、保护基团和高级 1H-NMR 现象
DOI：
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发表时间：
1997
期刊：
影响因子：
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通讯作者：
S. Kragerud
中科院分区：
文献类型：
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作者：
R. Brisbois;William G. Batterman;S. Kragerud
报道了一种制备和纯化四氢-2-(2-丙氧基)-2H-吡喃的方法，作为一种介绍性的有机实验室练习。目标化合物的合成说明了Markownikov加成和THP-醚保护基团的形成，产生了缩醛官能团，并模拟了最近开发的用于组合化学的树脂。通过闪蒸柱色谱纯化目标化合物使学生接触到现代合成方法学的核心技术。通过~1H核磁共振对目标化合物的分析引入了非一阶耦合(即AB四重态)和长程耦合(即4键)。
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.