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Facile Preparation of 3‐Acetamido‐5‐acetylfuran from N‐Acetyl‐d‐glucosamine by using Commercially Available Aluminum Salts
| Title: | Facile Preparation of 3‐Acetamido‐5‐acetylfuran from N‐Acetyl‐d‐glucosamine by using Commercially Available Aluminum Salts |
| Authors: | Daniele, Padovan Browse this author | | Hirokazu, Kobayashi Browse this author →KAKEN DB | | Atsushi, Fukuoka Browse this author →KAKEN DB |
| Keywords: | 3-acetamido-5-acetylfuran | | aluminum catalysis | | biomass valorization | | homogeneous catalysis | | N-acetylglucosamine dehydration |
| Issue Date: | 22-Jul-2020 |
| Publisher: | Wiley-Blackwell |
| Journal Title: | ChemSusChem |
| Volume: | 13 |
| Issue: | 14 |
| Start Page: | 3594 |
| End Page: | 3598 |
| Publisher DOI: | 10.1002/cssc.202001068 |
| Abstract: | 3-Acetamido-5-acetylfuran (3A5AF) is a promising intermediate obtained from chitin for the production of N-containing value-added chemicals. However, the synthetic method is complicated so far, which has limited further investigation using 3A5AF. Herein, a facile method was developed for synthesizing 3A5AF from N-acetyl-d-glucosamine (NAG), including a simple isolation procedure. A 30 % yield of 3A5AF was obtained by performing the dehydration of NAG in N,N-dimethylformamide (DMF) solvent in the presence of AlCl3.6 H2O at a temperature as low as 120 degrees C by conventional heating for 30 min. This method tolerated a wide range of temperature and concentration of substrate, thus easily allowing scale-up of the reaction. The produced 3A5AF was isolated with 98 % purity by simple column chromatography. Additionally, a highly functionalized N-containing lactone was identified as a byproduct under these reaction conditions. |
| Rights: | This is the peer reviewed version of the following article: D. Padovan, H. Kobayashi, A. Fukuoka, Facile Preparation of 3‐Acetamido‐5‐acetylfuran from N‐Acetyl‐d‐glucosamine by using Commercially Available Aluminum Salts, ChemSusChem 2020, 13, 3594, which has been published in final form at https://doi.org/10.1002/cssc.202001068 . This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/82288 |
| Appears in Collections: | 触媒科学研究所 (Institute for Catalysis) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 福岡 淳
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