(E)-[3-Methoxy-5-oxo-4-phenylfuran-2(5H)-ylidene]phenylacetic acid methyl ester

Base Information

• Chemical Name: (E)-[3-Methoxy-5-oxo-4-phenylfuran-2(5H)-ylidene]phenylacetic acid methyl ester
• CAS No.: 22628-22-4
• Molecular Formula: C20H16O5
• Molecular Weight: 336.344
• Mol file: 22628-22-4.mol

Synonyms:(E)-[3-Methoxy-5-oxo-4-phenylfuran-2(5H)-ylidene]phenylacetic acid methyl ester

Chemical Property of (E)-[3-Methoxy-5-oxo-4-phenylfuran-2(5H)-ylidene]phenylacetic acid methyl ester

Chemical Property:

• PSA: 61.83000
• LogP: 3.18520

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (E)-[3-Methoxy-5-oxo-4-phenylfuran-2(5H)-ylidene]phenylacetic acid methyl ester

There total 22 articles about (E)-[3-Methoxy-5-oxo-4-phenylfuran-2(5H)-ylidene]phenylacetic 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: 86.0%

phenylboronic acid (98-80-6) + (3-methoxy-5-oxo-4-trifluoromethanesulfonyloxy-5H-furan-2-ylidene)-phenyl-acetic acid methyl ester (704890-29-9) → (E)-4-methoxy-5-(α-methoxycarbonylbenzylidene)-3-phenylfuran-2(5H)-one (22628-22-4)

Guidance literature:

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; for 4h; Heating;

DOI:10.1021/jo049780a

Reference yield: 86.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + vulpic acid (521-52-8,73622-57-8) → (E)-4-methoxy-5-(α-methoxycarbonylbenzylidene)-3-phenylfuran-2(5H)-one (22628-22-4)

Guidance literature:

In diethyl ether; at 0 ℃; for 3h;

Reference yield:

benzeneacetic acid methyl ester (101-41-7) → (E)-4-methoxy-5-(α-methoxycarbonylbenzylidene)-3-phenylfuran-2(5H)-one (22628-22-4)

Guidance literature:

Multi-step reaction with 6 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

6.1: 86 percent / K₃PO₄ / Pd(PPh₃)4 / dioxane / 4 h / Heating

With pyridine; potassium phosphate; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; triethylamine; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; dichloromethane; benzene; 6.1: Suzuki cross-coupling reaction;

DOI:10.1021/jo049780a

upstream raw materials:

diazomethane

vulpic acid

methyl 2-oxo-2-phenylacetate

5-dimethoxyphosphoryl-4-methoxy-3-phenylfuran-2(5H)-one

Downstream raw materials:

vulpic acid

(E)-5-(α-carboxybenzylidene)-4-hydroxy-3-phenylfuran-2(5H)-one