Facile, Rapid, and High-Yield Synthesis of Pillar[5]arene from Commercially Available Reagents and Its X-ray Crystal Structure

We monitored the progress of formation of dimethoxypillar[5]arene by size-exclusion chromatography. Surprisingly, the cyclization reaction completely finished in just 3 min. By improving the reaction conditions and purification process, we successfully obtained dimethoxypillar[5]arene in a short tim...

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Bibliographic Details
Published in:Journal of organic chemistry 2011-01, Vol.76 (1), p.328-331
Main Authors: Ogoshi, Tomoki, Aoki, Takamichi, Kitajima, Keisuke, Fujinami, Shuhei, Yamagishi, Tada-aki, Nakamoto, Yoshiaki
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Summary:We monitored the progress of formation of dimethoxypillar[5]arene by size-exclusion chromatography. Surprisingly, the cyclization reaction completely finished in just 3 min. By improving the reaction conditions and purification process, we successfully obtained dimethoxypillar[5]arene in a short time and in high yield (71%) from commercially available reagents. By improving the deprotection reaction of the methoxy moieties, pillar[5]arene was isolated quantitatively. Single crystal X-ray analysis confirmed the structure of pillar[5]arene in the solid state.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo1020823