Preparation method of 3-aryl propiolic acid and 3-aryl propiolate compound
A technology of aryl propiolic acid ester and aryl propiolic acid, which is applied in the field of preparation of 3-aryl propiolic acid and 3-aryl propiolic acid ester compounds, can solve the problem of the lack of varieties of transition catalysts, the reaction System high pressure, substrate expansion range is small, etc., to avoid heavy metal residues, high reaction efficiency, and mild conditions
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Embodiment 1
[0054] Example 1: At 60°C, cesium carbonate participates in the reaction of phenylacetylene and carbon dioxide:
[0055] Under the airtight conditions of anhydrous, oxygen-free and argon protection, weigh 0.6516g Cs in the reaction bottle 2 CO 3 (2mmol, 2equiv.), add 110μL (1mmol, 1equiv.) phenylacetylene to the micro syringe, add 5mL DMSO to the syringe, CO 2 Gas replaced the air in the reaction system, and reacted at 60°C for 24h. After the reaction was completed, it was exposed to air, cooled slightly at room temperature, and then cooled with an ice-water bath. Add 10 mL of deionized water, then add 20 mL of 6mol / L HCl solution to fully acidify, extract with 3×10 mL of anhydrous ether, combine the organic phases, and wash the organic phases with saturated brine. Separate the organic phase and add anhydrous Na 2 SO 4 After drying, the solvent was removed under reduced pressure to obtain the target product with an isolated yield of 94%. The structure of the target produ...
Embodiment 2
[0060] Example 2: At 40°C, cesium carbonate participates in the reaction of phenylacetylene and carbon dioxide:
[0061] Under the airtight conditions of anhydrous, oxygen-free and argon protection, weigh 0.6516g Cs in the reaction bottle 2 CO 3 (2mmol, 2equiv.), add 110μL (1mmol, 1equiv.) phenylacetylene to the micro syringe, add 5mL DMSO to the syringe, CO 2 Gas replaced the air in the reaction system, and reacted at 40°C for 24h. After the reaction was completed, it was exposed to air, cooled slightly at room temperature, and then cooled with an ice-water bath. Add 10 mL of deionized water, then add 20 mL of 6mol / L HCl solution to fully acidify, extract with 3×10 mL of anhydrous ether, combine the organic phases, and wash the organic phases with saturated brine. Separate the organic phase and add anhydrous Na 2 SO 4 After drying, the solvent was removed under reduced pressure to obtain the target product with an isolated yield of 51%.
Embodiment 3
[0062] Example 3: At 50°C, cesium carbonate participates in the reaction of phenylacetylene and carbon dioxide:
[0063] Under the airtight conditions of anhydrous, oxygen-free and argon protection, weigh 0.6516g Cs in the reaction bottle 2 CO 3 (2mmol, 2equiv.), add 110μL (1mmol, 1equiv.) phenylacetylene to the micro syringe, add 5mL DMSO to the syringe, CO 2 Gas replaced the air in the reaction system, and reacted at 50°C for 24h. After the reaction was completed, it was exposed to air, cooled slightly at room temperature, and then cooled with an ice-water bath. Add 10 mL of deionized water, then add 20 mL of 6mol / L HCl solution to fully acidify, extract with 3×10 mL of anhydrous ether, combine the organic phases, and wash the organic phases with saturated brine. Separate the organic phase and add anhydrous Na 2 SO 4 After drying, the solvent was removed under reduced pressure to obtain the target product with an isolated yield of 70%.
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