Benzofuran derivatives. Part 4 , synthesis of benzofurans and 2,3,4,5-tetrahydro-1-benzoxepin-3,5-diones

By treatment of ethyl 4- or 5-substituted 2-acetylphenoxyacetates 1 with potassium hydroxide in dry dioxane, benzofurans 2–7 and 2,3,4,5-tetrahydro-1-benzoxepin-3,5-diones 8 were obtained. The relative yields of benzofurans 2–7 and 2,3,4,5-tetrahydro-1-benzoxepin-3,5-diones 8 varied with the types of 4- or 5-substituents. The electron-donating 4-methoxyl group favored the formation of benzoxepins. On the other hand, electron-withdrawing substituents such as the 4-nitro group favored the formation of benzofurans. When esters 1 were treated with sodium amide, 2,3-dihydrobenzofurans 2 were obtained exclusively regardless of 4- or 5-substituents.