Additional Nucleophile-Free FeCl<sub>3</sub>-Catalyzed Green Deprotection of 2,4-Dimethoxyphenylmethyl-Protected Alcohols and Carboxylic Acids
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- Sawama Yoshinari
- Gifu Pharmaceutical University
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- Masuda Masahiro
- Gifu Pharmaceutical University
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- Honda Akie
- Gifu Pharmaceutical University
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- Yokoyama Hiroki
- Gifu Pharmaceutical University
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- Park Kwihwan
- Gifu Pharmaceutical University
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- Yasukawa Naoki
- Gifu Pharmaceutical University
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- Monguchi Yasunari
- Gifu Pharmaceutical University
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- Sajiki Hironao
- Gifu Pharmaceutical University
Bibliographic Information
- Other Title
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- Additional Nucleophile-Free FeCl₃-Catalyzed Green Deprotection of 2,4-Dimethoxyphenylmethyl-Protected Alcohols and Carboxylic Acids
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Abstract
The deprotection of the methoxyphenylmethyl (MPM) ether and ester derivatives can be generally achieved by the combinatorial use of a catalytic Lewis acid and stoichiometric nucleophile. The deprotections of 2,4-dimethoxyphenylmethyl (DMPM)-protected alcohols and carboxylic acids were found to be effectively catalyzed by iron(III) chloride without any additional nucleophile to form the deprotected mother alcohols and carboxylic acids in excellent yields. Since the present deprotection proceeds via the self-assembling mechanism of the 2,4-DMPM protective group itself to give the hardly-soluble resorcinarene derivative as a precipitate, the rigorous purification process by silica-gel column chromatography was unnecessary and the sufficiently-pure alcohols and carboxylic acids were easily obtained in satisfactory yields after simple filtration.
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 64 (7), 778-784, 2016
The Pharmaceutical Society of Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390001204179132928
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- NII Article ID
- 130005160072
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- NII Book ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL BIB ID
- 027451482
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- PubMed
- 27373632
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- Abstract License Flag
- Disallowed