Synthesis of 5-hydroxy-N-(2-vinyloxyalkyl)indoles from dicarbonyl compounds and vinyloxyalkylamines was written by Kukharev, B. F.;Stankevich, V. K.;Klimenko, G. R.;Lobanova, N. A.. And the article was included in Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya) in 1997.Formula: C11H10O3 This article mentions the following:
N-(Vinyloxyalkyl) enamino ketones were obtained by the condensation of vinyloxyalkylamines with acetylacetone or Et acetoacetate. Their subsequent reactions with 1,4-benzoquinone produce the corresponding 5-hydroxy-2-methyl-N-(2-vinyloxyalkyl)indoles in 17-43% yields. The structures of the compounds obtained were confirmed by IR and 1H NMR spectroscopy. In the experiment, the researchers used many compounds, for example, 1-(5-Hydroxy-2-methylbenzofuran-3-yl)ethanone (cas: 28241-99-8Formula: C11H10O3).
1-(5-Hydroxy-2-methylbenzofuran-3-yl)ethanone (cas: 28241-99-8) belongs to benzofurans derivatives. Benzofurans are only weakly aromatic in nature and they are cleaved by many oxidative and reductive conditions. As benzofurans are prone to undergo ring opening of the heterocycle, examples of reduction of this type of aromatics by using dissolving metals are rather scarce.Formula: C11H10O3
Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem