Facile Preparation of 3‐Acetamido‐5‐acetylfuran from N‐Acetyl‐d‐glucosamine by using Commercially Available Aluminum Salts

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 H2 O at a temperature as low as 120 °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.