Microwave-Assisted Hydrolysis of Ethyl Azolylacetates and Cinnamates with K<sub>2</sub>CO<sub>3</sub>: Synthesis of Potassium Carboxylates

In this study, the hydrolysis of ethyl azolylacetates and ethyl cinnamates using K<sub>2</sub>CO<sub>3</sub>/ethanol under microwave irradiation was developed. For this purpose, ethyl azolylacetates were first synthesized by nucleophilic substitution between the corresponding azole and ethyl bromoacetate under sonication at 50 °C for 3 h, yielding derivatives with 10-92% chemical yields, while ethyl cinnamates were obtained by a microwave-assisted Horner-Wadsworth-Emmons (HWE) reaction of triethyl phosphonoacetate with a variety of aryl aldehydes at 140 °C for 20 min, yielding derivatives with moderate to high yields (67-98%). Initially, the optimization of the hydrolysis reaction was performed using ethyl pyrazolylacetate as a model starting material while varying the temperature, time, and base equivalents; the best results were achieved by carrying out the reaction at 180 °C for 20 min with 3.0 eq of K<sub>2</sub>CO<sub>3</sub>. This simple and greener method facilitated the synthesis of potassium carboxylates in moderate to high yields, 80-98% for azolyl derivatives and 73-98% for cinnamate derivatives. The structures of all potassium carboxylates were confirmed by FTIR, <sup>1</sup>H, <sup>13</sup>C NMR, and HRMS.

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Journal
ACS Omega
Published
2024-09-17
DOI
https://doi.org/10.1021/acsomega.4c05596
Citations
1
Primary Topic
Microwave-Assisted Synthesis and Applications
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article
Field-Weighted Citation Impact
0.25

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Microwave-Assisted Hydrolysis of Ethyl Azolylacetates and Cinnamates with K2CO3: Synthesis of Potassium Carboxylates

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1 citations
ACS Omega
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article

Microwave-Assisted Hydrolysis of Ethyl Azolylacetates and Cinnamates with K2CO3: Synthesis of Potassium Carboxylates

Verónica M. Rivas-Galindo, Eugenio Hernandez‐Fernandez, Susana López-Cortina, Mario Ordóñez, N. Tiempos-Flores, Jorge Hernández-Fernández, Katia Guadalupe García-Alvarez
article en
1 citations

Abstract

In this study, the hydrolysis of ethyl azolylacetates and ethyl cinnamates using K<sub>2</sub>CO<sub>3</sub>/ethanol under microwave irradiation was developed. For this purpose, ethyl azolylacetates were first synthesized by nucleophilic substitution between the corresponding azole and ethyl bromoacetate under sonication at 50 °C for 3 h, yielding derivatives with 10-92% chemical yields, while ethyl cinnamates were obtained by a microwave-assisted Horner-Wadsworth-Emmons (HWE) reaction of triethyl phosphonoacetate with a variety of aryl aldehydes at 140 °C for 20 min, yielding derivatives with moderate to high yields (67-98%). Initially, the optimization of the hydrolysis reaction was performed using ethyl pyrazolylacetate as a model starting material while varying the temperature, time, and base equivalents; the best results were achieved by carrying out the reaction at 180 °C for 20 min with 3.0 eq of K<sub>2</sub>CO<sub>3</sub>. This simple and greener method facilitated the synthesis of potassium carboxylates in moderate to high yields, 80-98% for azolyl derivatives and 73-98% for cinnamate derivatives. The structures of all potassium carboxylates were confirmed by FTIR, <sup>1</sup>H, <sup>13</sup>C NMR, and HRMS.

ACS OmegaVol. 9(39)
Universidad Autónoma de Nuevo León (MX), Universidad Autónoma del Estado de Morelos (MX)
Consejo Nacional de Ciencia y Tecnología, Universidad Autónoma de Nuevo León
Clean water and sanitation
Openalex Percentile: Top 48%
Microwave-Assisted Synthesis and Applications
0.25
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