5-[2-(4-chloro-phenyl)-4-methylene-5-oxo-tetrahydro-furan-2-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid

Base Information

• Chemical Name: 5-[2-(4-chloro-phenyl)-4-methylene-5-oxo-tetrahydro-furan-2-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid
• CAS No.: 692259-28-2
• Molecular Formula: C₁₇H₁₅ClN₂O₅
• Molecular Weight: 362.769
• Mol file: 692259-28-2.mol

Synonyms:5-[2-(4-chloro-phenyl)-4-methylene-5-oxo-tetrahydro-furan-2-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid

Chemical Property of 5-[2-(4-chloro-phenyl)-4-methylene-5-oxo-tetrahydro-furan-2-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[2-(4-chloro-phenyl)-4-methylene-5-oxo-tetrahydro-furan-2-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid

There total 6 articles about 5-[2-(4-chloro-phenyl)-4-methylene-5-oxo-tetrahydro-furan-2-ylmethoxy]-2-methyl-2H-pyrazole-3-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: 95.0%

5-[2-(4-chlorophenyl)-4-methylene-5-oxotetrahydrofuran-2-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid tert-butyl ester (692259-21-5) → 5-[2-(4-chloro-phenyl)-4-methylene-5-oxo-tetrahydro-furan-2-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid (692259-28-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/jm031104y

Reference yield:

4-chlorobenzoylmethyl bromide (536-38-9) → 5-[2-(4-chloro-phenyl)-4-methylene-5-oxo-tetrahydro-furan-2-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid (692259-28-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide / 1.5 h / 0 - 20 °C

1.2: 95 percent / dimethylformamide / 18 h / 20 °C

2.1: 92 percent / aq. LiOH / tetrahydrofuran; methanol / 1 h / 20 °C

3.1: BTEAC; K₂CO₃ / dimethylformamide / 24 h / 55 °C

4.1: 280 mg / Zn; hydroquinone / tetrahydrofuran / 24 h / Heating

5.1: 95 percent / CF₃COOH / CH₂Cl₂ / 3 h / 20 °C

With lithium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; sodium hydride; potassium carbonate; hydroquinone; trifluoroacetic acid; zinc; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 4.1: Reformatsky-type condensation;

DOI:10.1021/jm031104y

Reference yield:

5-hydroxy-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (52867-42-2) → 5-[2-(4-chloro-phenyl)-4-methylene-5-oxo-tetrahydro-furan-2-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid (692259-28-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide / 1.5 h / 0 - 20 °C

1.2: 95 percent / dimethylformamide / 18 h / 20 °C

2.1: 92 percent / aq. LiOH / tetrahydrofuran; methanol / 1 h / 20 °C

3.1: BTEAC; K₂CO₃ / dimethylformamide / 24 h / 55 °C

4.1: 280 mg / Zn; hydroquinone / tetrahydrofuran / 24 h / Heating

5.1: 95 percent / CF₃COOH / CH₂Cl₂ / 3 h / 20 °C

With lithium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; sodium hydride; potassium carbonate; hydroquinone; trifluoroacetic acid; zinc; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 4.1: Reformatsky-type condensation;

DOI:10.1021/jm031104y

upstream raw materials:

5-[2-(4-chlorophenyl)-4-methylene-5-oxotetrahydrofuran-2-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid tert-butyl ester

4-chlorobenzoylmethyl bromide

5-hydroxy-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester

5-[2-(4-chlorophenyl)-2-oxoethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid