(R/S)-Ethyl 2-Acetoxy-4-phenyl-4H-chromene-3-carboxylate

A simple protocol for the preparation of O-acylated enol form (R/S)-ethyl-2-acetoxy-4-phenyl-4H-chromene-3-carboxylate 5 was presented. The compound was characterized by 1H-, 13C-and DEPT135 NMR spectra, including {1H,1H} COSY, {1H,13C} HSQC, {1H,13C} HMBC, and 2D-NOESY spectra. The preferred regioselectivity for O-acylation of 3,4-dihydrocoumarin 5 in the presence of substituent in the 4th position in the chroman ring and accounting for the steric hindrance of the ester group in the 3rd place was confirmed.

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Publication Details

Journal
Molbank
Published
2024-08-26
DOI
https://doi.org/10.3390/m1875
Primary Topic
Synthesis of Organic Compounds
Type
article
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article

(R/S)-Ethyl 2-Acetoxy-4-phenyl-4H-chromene-3-carboxylate

Ana I. Koleva, Rositca D. Nikolova, Nevena I. Petkova‐Yankova
Molbank
Synthesis of Organic Compounds
article

(R/S)-Ethyl 2-Acetoxy-4-phenyl-4H-chromene-3-carboxylate

Ana I. Koleva, Rositca D. Nikolova, Nevena I. Petkova‐Yankova
article en

Abstract

A simple protocol for the preparation of O-acylated enol form (R/S)-ethyl-2-acetoxy-4-phenyl-4H-chromene-3-carboxylate 5 was presented. The compound was characterized by 1H-, 13C-and DEPT135 NMR spectra, including {1H,1H} COSY, {1H,13C} HSQC, {1H,13C} HMBC, and 2D-NOESY spectra. The preferred regioselectivity for O-acylation of 3,4-dihydrocoumarin 5 in the presence of substituent in the 4th position in the chroman ring and accounting for the steric hindrance of the ester group in the 3rd place was confirmed.

MolbankVol. 2024(3)
Sofia University "St. Kliment Ohridski" (BG)
Clean water and sanitation
Openalex Percentile: Top 86%
Synthesis of Organic Compounds
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