5-[2-(ethoxy)carbonyl-5-(4-fluorophenyl)-3-oxo-1-penten-1-yl] thiophene-2-carboxylic acid

Base Information

• Chemical Name: 5-[2-(ethoxy)carbonyl-5-(4-fluorophenyl)-3-oxo-1-penten-1-yl] thiophene-2-carboxylic acid
• CAS No.: 858671-10-0
• Molecular Formula: C₁₉H₁₇FO₅S
• Molecular Weight: 376.405

Synonyms:5-[2-(ethoxy)carbonyl-5-(4-fluorophenyl)-3-oxo-1-penten-1-yl] thiophene-2-carboxylic acid

Chemical Property of 5-[2-(ethoxy)carbonyl-5-(4-fluorophenyl)-3-oxo-1-penten-1-yl] thiophene-2-carboxylic acid

Chemical Property:

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Technology Process of 5-[2-(ethoxy)carbonyl-5-(4-fluorophenyl)-3-oxo-1-penten-1-yl] thiophene-2-carboxylic acid

There total 3 articles about 5-[2-(ethoxy)carbonyl-5-(4-fluorophenyl)-3-oxo-1-penten-1-yl] thiophene-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 34.0%

5-(4-Fluoro-phenyl)-3-oxo-pentanoic acid ethyl ester (498532-06-2) + 5-formyl-2-thiophencarboxylic acid (4565-31-5) → 5-[2-(ethoxy)carbonyl-5-(4-fluorophenyl)-3-oxo-1-penten-1-yl] thiophene-2-carboxylic acid (858671-10-0)

Guidance literature:

With piperidine; In benzene; Heating;

DOI:10.1021/jo050370b

Reference yield:

5-[3-(4-fluorophenyl)propanoyl]-2,2-dimethyl-1,3-dioxane-4,6-dione (603999-08-2) → 5-[2-(ethoxy)carbonyl-5-(4-fluorophenyl)-3-oxo-1-penten-1-yl] thiophene-2-carboxylic acid (858671-10-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / ethanol / 3 h / Heating

2: 34 percent / piperidine / benzene / Heating

With piperidine; ethanol; In benzene; 2: Knoevenagel reaction;

DOI:10.1021/jo050370b

Reference yield:

3-(4-fluorophenyl)propanoic acid (459-31-4) → 5-[2-(ethoxy)carbonyl-5-(4-fluorophenyl)-3-oxo-1-penten-1-yl] thiophene-2-carboxylic acid (858671-10-0)

Guidance literature:

Multi-step reaction with 3 steps

1: DMAP; DCC / CH₂Cl₂ / 20 °C

2: 54 percent / ethanol / 3 h / Heating

3: 34 percent / piperidine / benzene / Heating

With piperidine; dmap; ethanol; dicyclohexyl-carbodiimide; In dichloromethane; benzene; 3: Knoevenagel reaction;

DOI:10.1021/jo050370b

upstream raw materials:

5-(4-Fluoro-phenyl)-3-oxo-pentanoic acid ethyl ester

5-formyl-2-thiophencarboxylic acid

5-[3-(4-fluorophenyl)propanoyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

3-(4-fluorophenyl)propanoic acid

Downstream raw materials:

5-{3-[(ethoxy)carbonyl]-2-[2-(4-fluorophenyl)ethyl]-5-oxo-8,9-dihydro-5H,7H-pyrazolo[1',2':1,2]pyrazolo[3,4-b]pyridin-4-yl}thiophene-2-carboxylic acid

5-{3-[(ethoxy)carbonyl]-2-[2-(4-fluorophenyl)ethyl]-5-oxo-1,5,8,9-tetrahydro-4H,7H-pyrazolo[1',2':1,2]pyrazolo[3,4-b]pyridin-4-yl}thiophene-2-carboxylic acid

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