Formation of a Renewable Amine and an Alcohol via Transformations of 3-Acetamido-5-acetylfuran

Abstract

The reactivity of the renewable amide 3-acetamido-5-acetylfuran (3A5AF) was explored. Hydrolysis of the amido group to yield the amino-substituted furan, 2-acetyl-4-aminofuran ( 1 ), was achieved via NaOH catalysis. Reduction of the acetyl group could be achieved stoichiometrically using NaBH 4 or catalytically via transfer hydrogenation using an Ir catalyst. The product alcohol, 3-acetamido-5-(1-hydroxylethyl)furan ( 2 ), underwent dehydration during analysis via GC-MS to yield an alkene ( 3 ). The potential reactivity of 3A5AF and 1 toward carbon dioxide was studied, but no reaction was observed due to the inherent acidity of 3A5AF and 1 despite the latter being an amine. The computationally determined p K a values for 3A5AF and 1 are reported. Interestingly, in this work, tautomerism of 3A5AF was observed in CD 3 OD as evidenced by H–D exchange within the acetyl group.