Optimization of the Selective Monohydrolysis of Diethyl 4-Aryl-4H-pyran-3,5-dicarboxylates
A simple, efficient and eco-friendly procedure for the selective monohydrolysis of diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylates under quaternary ammonium salt catalysis conditions is presented. The catalytic activities of various quaternary ammonium salts were investigated using different...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2011-05-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/16/5/3845/ |
| _version_ | 1818172072557281280 |
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| author | Hong Yan Xiuqing Song Xiaohui Song Jiaojiao Duan |
| author_facet | Hong Yan Xiuqing Song Xiaohui Song Jiaojiao Duan |
| author_sort | Hong Yan |
| collection | DOAJ |
| description | A simple, efficient and eco-friendly procedure for the selective monohydrolysis of diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylates under quaternary ammonium salt catalysis conditions is presented. The catalytic activities of various quaternary ammonium salts were investigated using different molar ratios of NaOH and water-organic solvent mixtures. The results indicate that the combination of 1.0 equivalent of tetraethyl-ammonium bromide (TEAB) with 1.2 equivalents of NaOH in a 10% water-ethanol media at 40 °C displays remarkable selectivity for the monohydrolysis of diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylates. The utility of this process is demonstrated by the monohydrolysis of a series of 4-aryl-4H-pyran-3,5-dicarboxylate esters to afford the corresponding monoesters in 20–80% yields under the optimized conditions. |
| first_indexed | 2024-12-11T19:06:48Z |
| format | Article |
| id | doaj.art-8d00d5c9f9174c41bd98abeaf49d63e3 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T19:06:48Z |
| publishDate | 2011-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-8d00d5c9f9174c41bd98abeaf49d63e32022-12-22T00:53:53ZengMDPI AGMolecules1420-30492011-05-011653845385410.3390/molecules16053845Optimization of the Selective Monohydrolysis of Diethyl 4-Aryl-4H-pyran-3,5-dicarboxylatesHong YanXiuqing SongXiaohui SongJiaojiao DuanA simple, efficient and eco-friendly procedure for the selective monohydrolysis of diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylates under quaternary ammonium salt catalysis conditions is presented. The catalytic activities of various quaternary ammonium salts were investigated using different molar ratios of NaOH and water-organic solvent mixtures. The results indicate that the combination of 1.0 equivalent of tetraethyl-ammonium bromide (TEAB) with 1.2 equivalents of NaOH in a 10% water-ethanol media at 40 °C displays remarkable selectivity for the monohydrolysis of diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylates. The utility of this process is demonstrated by the monohydrolysis of a series of 4-aryl-4H-pyran-3,5-dicarboxylate esters to afford the corresponding monoesters in 20–80% yields under the optimized conditions.http://www.mdpi.com/1420-3049/16/5/3845/monohydrolysis4-aryl-4H-pyranquaternary ammonium saltmonoestersymmetric diester |
| spellingShingle | Hong Yan Xiuqing Song Xiaohui Song Jiaojiao Duan Optimization of the Selective Monohydrolysis of Diethyl 4-Aryl-4H-pyran-3,5-dicarboxylates Molecules monohydrolysis 4-aryl-4H-pyran quaternary ammonium salt monoester symmetric diester |
| title | Optimization of the Selective Monohydrolysis of Diethyl 4-Aryl-4H-pyran-3,5-dicarboxylates |
| title_full | Optimization of the Selective Monohydrolysis of Diethyl 4-Aryl-4H-pyran-3,5-dicarboxylates |
| title_fullStr | Optimization of the Selective Monohydrolysis of Diethyl 4-Aryl-4H-pyran-3,5-dicarboxylates |
| title_full_unstemmed | Optimization of the Selective Monohydrolysis of Diethyl 4-Aryl-4H-pyran-3,5-dicarboxylates |
| title_short | Optimization of the Selective Monohydrolysis of Diethyl 4-Aryl-4H-pyran-3,5-dicarboxylates |
| title_sort | optimization of the selective monohydrolysis of diethyl 4 aryl 4h pyran 3 5 dicarboxylates |
| topic | monohydrolysis 4-aryl-4H-pyran quaternary ammonium salt monoester symmetric diester |
| url | http://www.mdpi.com/1420-3049/16/5/3845/ |
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