2024-03-28T11:57:42Zhttps://eprints.lib.hokudai.ac.jp/dspace-oai/requestoai:eprints.lib.hokudai.ac.jp:2115/822882022-11-17T02:08:08Zhdl_2115_20059hdl_2115_151Facile Preparation of 3‐Acetamido‐5‐acetylfuran from N‐Acetyl‐d‐glucosamine by using Commercially Available Aluminum SaltsDaniele, Padovan1000030545968Hirokazu, Kobayashi1000080189927Atsushi, Fukuokaopen accessThis 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.3-acetamido-5-acetylfuranaluminum catalysisbiomass valorizationhomogeneous catalysisN-acetylglucosamine dehydration4313-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.Wiley-Blackwell2020-07-22engjournal articleAMhttp://hdl.handle.net/2115/82288https://doi.org/10.1002/cssc.2020010681864-5631ChemSusChem131435943598https://eprints.lib.hokudai.ac.jp/dspace/bitstream/2115/82288/1/manuscript.pdfapplication/pdf394.59 KB2020-07-22https://eprints.lib.hokudai.ac.jp/dspace/bitstream/2115/82288/2/supporting%20information.pdfapplication/pdf1.62 MB2020-07-22