Zeolite-catalyzed acylation of heterocyclic compounds — VI. One-step synthesis of 3-(benzofuran-2-carbonyl)pentane-2,4-dione from 2-acetylbenzofuran over HY-zeolite

Zeolite-catalyzed acylation of heterocyclic compounds — VI. One-step synthesis of 3-(benzofuran-2-carbonyl)pentane-2,4-dione from 2-acetylbenzofuran over HY-zeolite

The reaction between 2-acetylbenzofuran and acetic anhydride at 60°C in the presence of HY-zeolite ( Si Al = 16 ) led to a single final product: 3-(benzofuran-2-carbonyl)pentane-2,4-dione resulting from two consecutive acylation steps on the side chain. It was obtained in a 90% purity at around 50%...

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Veröffentlicht in:Tetrahedron 1998-12, Vol.54 (49), p.14757-14766
Hauptverfasser: Richard, F., Carreyre, H., Coustard, J.M., Bachmann, C., Perot, G.
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container_end_page 14766
container_issue 49
container_start_page 14757
container_title Tetrahedron
container_volume 54
creator Richard, F.
Carreyre, H.
Coustard, J.M.
Bachmann, C.
Perot, G.
description The reaction between 2-acetylbenzofuran and acetic anhydride at 60°C in the presence of HY-zeolite ( Si Al = 16 ) led to a single final product: 3-(benzofuran-2-carbonyl)pentane-2,4-dione resulting from two consecutive acylation steps on the side chain. It was obtained in a 90% purity at around 50% conversion of 2-acetylbenzofuran. Other minor products and intermediates were also identified. A mechanism is proposed to account for the formation of the various products. The catalyst can be regenerated and reused.
doi_str_mv 10.1016/S0040-4020(98)00904-1
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title Zeolite-catalyzed acylation of heterocyclic compounds — VI. One-step synthesis of 3-(benzofuran-2-carbonyl)pentane-2,4-dione from 2-acetylbenzofuran over HY-zeolite
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