Article

Facile, rapid, and high-yield synthesis of pillar[5]arene from commercially available reagents and its X-ray crystal structure.

Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
The Journal of Organic Chemistry (impact factor: 4.45). 01/2011; 76(1):328-31. DOI:10.1021/jo1020823 pp.328-31
Source: PubMed

ABSTRACT 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.

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Keywords

3 min
 
cyclization reaction
 
deprotection reaction
 
purification process
 
quantitatively
 
reaction conditions
 
short time
 
size-exclusion chromatography
 
solid state
 

Tomoki Ogoshi