Unexpected Truce–Smiles type rearrangement of 2-(2′-pyridyloxy) phenylacetic esters: synthesis of 3-pyridyl-2-benzofuranones

Enolization of 2-(2′-pyridyloxy)phenylacetic acid esters with either potassium or sodium hydride induced a Truce–Smiles rearrangement, producing pyridine substituted 2-benzofuranones. Rearrangement of a 2-(4-nitrophenoxy)phenylacetate and a 2-(2′-pyrimidyloxy)phenylacetate produced similar results.