(3-methoxy-5-oxo-4-trifluoromethanesulfonyloxy-5H-furan-2-ylidene)-phenyl-acetic acid methyl ester

Base Information

• Chemical Name: (3-methoxy-5-oxo-4-trifluoromethanesulfonyloxy-5H-furan-2-ylidene)-phenyl-acetic acid methyl ester
• CAS No.: 704890-29-9
• Molecular Formula: C₁₅H₁₁F₃O₈S
• Molecular Weight: 408.309
• Mol file: 704890-29-9.mol

Synonyms:(3-methoxy-5-oxo-4-trifluoromethanesulfonyloxy-5H-furan-2-ylidene)-phenyl-acetic acid methyl ester

Chemical Property of (3-methoxy-5-oxo-4-trifluoromethanesulfonyloxy-5H-furan-2-ylidene)-phenyl-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3-methoxy-5-oxo-4-trifluoromethanesulfonyloxy-5H-furan-2-ylidene)-phenyl-acetic acid methyl ester

There total 5 articles about (3-methoxy-5-oxo-4-trifluoromethanesulfonyloxy-5H-furan-2-ylidene)-phenyl-acetic acid methyl 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: 61.0%

trifluoromethylsulfonic anhydride (358-23-6) + (4-hydroxy-3-methoxy-5-oxo-5H-furan-2-ylidene)-phenyl-acetic acid methyl ester (704890-28-8) → (3-methoxy-5-oxo-4-trifluoromethanesulfonyloxy-5H-furan-2-ylidene)-phenyl-acetic acid methyl ester (704890-29-9)

Guidance literature:

With pyridine; at -78 - -10 ℃; for 4h;

DOI:10.1021/jo049780a

Reference yield:

benzeneacetic acid methyl ester (101-41-7) → (3-methoxy-5-oxo-4-trifluoromethanesulfonyloxy-5H-furan-2-ylidene)-phenyl-acetic acid methyl ester (704890-29-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: LDA / tetrahydrofuran / 1 h / -78 °C

1.2: 67 percent / tetrahydrofuran / 12 h / -78 - 20 °C

2.1: 84 percent / Et₃N / benzene / 72 h

3.1: LDA / tetrahydrofuran / 1 h / -78 °C

3.2: 90 percent / tetrahydrofuran / 12 h / 20 °C

4.1: 54 percent / (COCl)2; Me₃SiOTf / CH₂Cl₂ / 14 h / -78 - 20 °C

5.1: 61 percent / pyridine / 4 h / -78 - -10 °C

With pyridine; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1021/jo049780a

Reference yield:

4-methoxy-3-oxo-2-phenyl-butyric acid methyl ester (704890-25-5) → (3-methoxy-5-oxo-4-trifluoromethanesulfonyloxy-5H-furan-2-ylidene)-phenyl-acetic acid methyl ester (704890-29-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 84 percent / Et₃N / benzene / 72 h

2.1: LDA / tetrahydrofuran / 1 h / -78 °C

2.2: 90 percent / tetrahydrofuran / 12 h / 20 °C

3.1: 54 percent / (COCl)2; Me₃SiOTf / CH₂Cl₂ / 14 h / -78 - 20 °C

4.1: 61 percent / pyridine / 4 h / -78 - -10 °C

With pyridine; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1021/jo049780a

upstream raw materials:

trifluoromethylsulfonic anhydride

(4-hydroxy-3-methoxy-5-oxo-5H-furan-2-ylidene)-phenyl-acetic acid methyl ester

benzeneacetic acid methyl ester

4-methoxy-3-oxo-2-phenyl-butyric acid methyl ester

Downstream raw materials:

(E)-4-methoxy-5-(α-methoxycarbonylbenzylidene)-3-phenylfuran-2(5H)-one

(E)-4-hydroxy-5-(α-methoxycarbonylbenzylidene)-3-(4-methoxyphenyl)furan-2(5H)-one

(E)-4-methoxy-5-(α-methoxycarbonylbenzylidene)-3-(4-methoxyphenyl)furan-2(5H)-one