4-[6-((E)-3-ethoxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid ethyl ester

Base Information

• Chemical Name: 4-[6-((E)-3-ethoxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid ethyl ester
• CAS No.: 1297310-86-1
• Molecular Formula: C₂₇H₂₄FNO₇
• Molecular Weight: 493.488
• Mol file: 1297310-86-1.mol

Synonyms:4-[6-((E)-3-ethoxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid ethyl ester

Chemical Property of 4-[6-((E)-3-ethoxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[6-((E)-3-ethoxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid ethyl ester

There total 2 articles about 4-[6-((E)-3-ethoxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid ethyl ester 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: 79.0%

(E)-ethyl [3-acetyl-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-6-yl]acrylate (1297310-96-3) + oxalic acid diethyl ester (95-92-1) → 4-[6-((E)-3-ethoxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid ethyl ester (1297310-86-1)

Guidance literature:

(E)-ethyl [3-acetyl-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-6-yl]acrylate; oxalic acid diethyl ester; With sodium ethanolate; In N,N-dimethyl-formamide; at 20 ℃; for 20h; Inert atmosphere;

With hydrogenchloride; In water; for 0.5h;

DOI:10.1016/j.ejmech.2011.02.028

Reference yield:

3-acetyl-6-bromo-1-((4-fluorophenyl)methyl)-4(1H)-quinolinone (1187551-48-9) + ethyl acrylate (140-88-5,9003-32-1) → 4-[6-((E)-3-ethoxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid ethyl ester (1297310-86-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: palladium diacetate; triethylamine; triphenylphosphine / N,N-dimethyl-formamide / 48 h / 80 °C / Inert atmosphere

2.1: sodium ethanolate / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

2.2: 0.5 h

With sodium ethanolate; palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; 1.1: Heck reaction;

DOI:10.1016/j.ejmech.2011.02.028

Reference yield: 70.0%

4-[6-((E)-3-ethoxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid ethyl ester (1297310-86-1) → 4-[6-((E)-3-hydroxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid (1297310-88-3)

Guidance literature:

4-[6-((E)-3-ethoxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid ethyl ester; With methanol; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; methanol; water; pH=2; Cooling with ice;

DOI:10.1016/j.ejmech.2011.02.028

upstream raw materials:

3-acetyl-6-bromo-1-((4-fluorophenyl)methyl)-4(1H)-quinolinone

ethyl acrylate

(E)-ethyl [3-acetyl-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-6-yl]acrylate

oxalic acid diethyl ester

Downstream raw materials:

4-[6-((E)-3-hydroxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid