ethyl (2E)-3-(4-formyl-1-phenyl-1H-pyrazol-3-yl)acrylate

Base Information

• Chemical Name: ethyl (2E)-3-(4-formyl-1-phenyl-1H-pyrazol-3-yl)acrylate
• CAS No.: 1354413-60-7
• Molecular Formula: C₁₅H₁₄N₂O₃
• Molecular Weight: 270.288
• Mol file: 1354413-60-7.mol

Synonyms:ethyl (2E)-3-(4-formyl-1-phenyl-1H-pyrazol-3-yl)acrylate

Chemical Property of ethyl (2E)-3-(4-formyl-1-phenyl-1H-pyrazol-3-yl)acrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2E)-3-(4-formyl-1-phenyl-1H-pyrazol-3-yl)acrylate

There total 6 articles about ethyl (2E)-3-(4-formyl-1-phenyl-1H-pyrazol-3-yl)acrylate 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: 37.0%

4-formyl-1-phenyl-1H-pyrazol-3-yl trifluoromethanesulfonate (1354413-51-6) + ethyl acrylate (140-88-5,9003-32-1) → ethyl (2E)-3-(4-formyl-1-phenyl-1H-pyrazol-3-yl)acrylate (1354413-60-7)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; triethylamine; In N,N-dimethyl-formamide; at 100 ℃; for 9h; Inert atmosphere;

DOI:10.3998/ark.5550190.0012.b01

Reference yield:

1-phenyl-1H-pyrazol-3-ol (1008-79-3) → ethyl (2E)-3-(4-formyl-1-phenyl-1H-pyrazol-3-yl)acrylate (1354413-60-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: bromine / chloroform / 20 h / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

2.2: 1 h / 60 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / toluene / 48 h / 20 °C

5.1: triethylamine / dichloromethane / 1 h / 20 °C

6.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 9 h / 100 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; n-butyllithium; bromine; sodium hydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; mineral oil; 6.1: Heck cross-coupling reaction;

DOI:10.3998/ark.5550190.0012.b01

Reference yield:

3-(benzyloxy)-4-bromo-1-phenyl-1H-pyrazole (1354413-49-2) → ethyl (2E)-3-(4-formyl-1-phenyl-1H-pyrazol-3-yl)acrylate (1354413-60-7)

Guidance literature:

Multi-step reaction with 4 steps

1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - 20 °C / Inert atmosphere

2: trifluoroacetic acid / toluene / 48 h / 20 °C

3: triethylamine / dichloromethane / 1 h / 20 °C

4: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 9 h / 100 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; n-butyllithium; triethylamine; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 4: Heck cross-coupling reaction;

DOI:10.3998/ark.5550190.0012.b01

upstream raw materials:

3-(benzyloxy)-4-bromo-1-phenyl-1H-pyrazole

3-(benzyloxy)-1-phenyl-1H-pyrazole-4-carbaldehyde

4-formyl-1-phenyl-1H-pyrazol-3-yl trifluoromethanesulfonate

ethyl acrylate