3-Ethoxycarbonyl-1,4-benzodioxin-2-carboxylic acid, a novel 2,3-disubstituted benzodioxin, was prepared from readily available 1,4-benzodioxin-2-carboxylic acid by lithiation at C(3) and a reaction with the electrophile ethyl chloroformate. The analytical characterization of the product was performed via IR, 1H-NMR, 13C-NMR, HRMS, and HPLC-UV. Due to the unsymmetrically disubstituted unsaturation, the obtained monoester of 1,4-benzodioxin-2,3-dicarboxylic acid is a building block of great potential in the synthesis of a variety of compounds containing the benzodioxin or benzodioxane scaffold.

3-Ethoxycarbonyl-1,4-benzodioxin-2-carboxylic Acid / E. Armano, A. Giraudo, C. Morano, M. Pallavicini, C. Bolchi. - In: MOLBANK. - ISSN 1422-8599. - 2024:3(2024 Sep), pp. M1873.1-M1873.4. [10.3390/M1873]

3-Ethoxycarbonyl-1,4-benzodioxin-2-carboxylic Acid

E. Armano
Primo
;
A. Giraudo
Secondo
;
C. Morano;M. Pallavicini
Penultimo
;
C. Bolchi
Ultimo
2024

Abstract

3-Ethoxycarbonyl-1,4-benzodioxin-2-carboxylic acid, a novel 2,3-disubstituted benzodioxin, was prepared from readily available 1,4-benzodioxin-2-carboxylic acid by lithiation at C(3) and a reaction with the electrophile ethyl chloroformate. The analytical characterization of the product was performed via IR, 1H-NMR, 13C-NMR, HRMS, and HPLC-UV. Due to the unsymmetrically disubstituted unsaturation, the obtained monoester of 1,4-benzodioxin-2,3-dicarboxylic acid is a building block of great potential in the synthesis of a variety of compounds containing the benzodioxin or benzodioxane scaffold.
1,4-benzodioxin; 3-ethoxycarbonyl-1,4-benzodioxin-2-carboxylic acid; ethoxycarbonylation; ethyl chloroformate; lithiation;
Settore CHEM-07/A - Chimica farmaceutica
Settore CHEM-05/A - Chimica organica
set-2024
19-ago-2024
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/1107058
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