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.
Authors
- Verónica M. Rivas-Galindo (ORCID: https://orcid.org/0000-0002-7981-3674)
- Eugenio Hernandez‐Fernandez
- Susana López-Cortina (ORCID: https://orcid.org/0000-0002-4210-7848)
- Mario Ordóñez (ORCID: https://orcid.org/0000-0001-9395-7079)
- N. Tiempos-Flores (ORCID: https://orcid.org/0009-0001-1275-8316)
- Jorge Hernández-Fernández
- Katia Guadalupe García-Alvarez
Institutions
- Universidad Autónoma de Nuevo León (MX)
- Universidad Autónoma del Estado de Morelos (MX)
Publication Details
- Journal
- ACS Omega
- Published
- 2024-09-17
- DOI
- https://doi.org/10.1021/acsomega.4c05596
- Citations
- 1
- Primary Topic
- Microwave-Assisted Synthesis and Applications
- Type
- article
- Field-Weighted Citation Impact
- 0.25
Funders
- Consejo Nacional de Ciencia y Tecnología
- Universidad Autónoma de Nuevo León