2-Oxo-2<i>H</i>-chromen-7-yl 3-methylbutanoate

The title compound, C<sub>14</sub>H<sub>14</sub>O<sub>4</sub>, was synthesized by <i>O</i>-acyl-ation of umbelliferone with isovaleryl chloride in the presence of diethyl ether as a solvent and pyridine as a base. The side chain moiety <i>i.e.</i> the acetate fragment linking to the methyl-ethyl group is almost orthogonal to the almost planar (r.m.s deviation = 0.020 Å) coumarin ring system, making an angle of 76.26 (7)°. In the crystal, the mol-ecules form centrosymmetric dimers through pairwise C-H⋯O hydrogen bonds, generating <i>R</i> <sub>2</sub> <sup>2</sup>(8) and <i>R</i> <sub>2</sub> <sup>2</sup>(18) loops that lie within the crystallographic <i>ac</i> plane and propagate along the [001] direction.

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IUCrData
Published
2025-02-28
DOI
https://doi.org/10.1107/s2414314625001610
Primary Topic
Synthesis of Organic Compounds
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article
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article

2-Oxo-2H-chromen-7-yl 3-methylbutanoate

Akoun Abou, Ludovic Akonan, Abdoulaye Djandé, Pierre Francotte et al.
IUCrData
Synthesis of Organic Compounds
article

2-Oxo-2H-chromen-7-yl 3-methylbutanoate

Akoun Abou, Ludovic Akonan, Abdoulaye Djandé, Pierre Francotte, Hypolite Bazié
article en

Abstract

The title compound, C<sub>14</sub>H<sub>14</sub>O<sub>4</sub>, was synthesized by <i>O</i>-acyl-ation of umbelliferone with isovaleryl chloride in the presence of diethyl ether as a solvent and pyridine as a base. The side chain moiety <i>i.e.</i> the acetate fragment linking to the methyl-ethyl group is almost orthogonal to the almost planar (r.m.s deviation = 0.020 Å) coumarin ring system, making an angle of 76.26 (7)°. In the crystal, the mol-ecules form centrosymmetric dimers through pairwise C-H⋯O hydrogen bonds, generating <i>R</i> <sub>2</sub> <sup>2</sup>(8) and <i>R</i> <sub>2</sub> <sup>2</sup>(18) loops that lie within the crystallographic <i>ac</i> plane and propagate along the [001] direction.

IUCrDataVol. 10(2)
Université Joseph Ki-Zerbo (BF), University of Liège (BE), Université Nangui Abrogoua (CI), Institut National Polytechnique Félix Houphouët-Boigny (CI)
Clean water and sanitation
Openalex Percentile: Top 95%
Synthesis of Organic Compounds
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2-Oxo-2<i>H</i>-chromen-7-yl 3-methylbutanoate — Akoun Abou, Ludovic Akonan, et al. · IUCrData (2025) | TGRS Research Map | TGRS