Methyl (2E)-3-[7-methoxy-2-[3-methoxy-4-(phenylmethoxy)phenyl]-5-benzofuranyl]-2-propenoate

Base Information

• Chemical Name: Methyl (2E)-3-[7-methoxy-2-[3-methoxy-4-(phenylmethoxy)phenyl]-5-benzofuranyl]-2-propenoate
• CAS No.: 144735-55-7
• Molecular Formula: C₂₇H₂₄O₆
• Molecular Weight: 444.484
• DSSTox Substance ID: DTXSID401121384
• Mol file: 144735-55-7.mol

Synonyms:DTXSID401121384;Methyl (2E)-3-[7-methoxy-2-[3-methoxy-4-(phenylmethoxy)phenyl]-5-benzofuranyl]-2-propenoate;144735-55-7

Chemical Property of Methyl (2E)-3-[7-methoxy-2-[3-methoxy-4-(phenylmethoxy)phenyl]-5-benzofuranyl]-2-propenoate

Chemical Property:

• XLogP3: 5.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 444.15728848
• Heavy Atom Count: 33
• Complexity: 645

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC(=CC2=C1OC(=C2)C3=CC(=C(C=C3)OCC4=CC=CC=C4)OC)C=CC(=O)OC
• Isomeric SMILES: COC1=CC(=CC2=C1OC(=C2)C3=CC(=C(C=C3)OCC4=CC=CC=C4)OC)/C=C/C(=O)OC

Technology Process of Methyl (2E)-3-[7-methoxy-2-[3-methoxy-4-(phenylmethoxy)phenyl]-5-benzofuranyl]-2-propenoate

There total 14 articles about Methyl (2E)-3-[7-methoxy-2-[3-methoxy-4-(phenylmethoxy)phenyl]-5-benzofuranyl]-2-propenoate 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: 67.0%

methyl 3-methoxy-4-hydroxy-5-bromo-cinnamate (146072-13-1) + cuprous (4-benzyloxy-3-methoxy)phenyl acetylide (135040-84-5) → 5-(2-(methoxycarbonyl)trans-ethenyl)-7-methoxy-2-(3'-methoxy-4'-(benzyloxy)phenyl)benzofuran (144735-55-7)

Guidance literature:

With pyridine; at 120 ℃;

DOI:10.1016/S0040-4039(00)78908-8

Reference yield: 50.0%

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) + 2-[4-(benzyloxy)-3-methoxyphenyl]-5-bromo-7-methoxybenzofuran (515814-05-8) → 5-(2-(methoxycarbonyl)trans-ethenyl)-7-methoxy-2-(3'-methoxy-4'-(benzyloxy)phenyl)benzofuran (144735-55-7)

Guidance literature:

With palladium diacetate; potassium carbonate; triphenylphosphine; In acetonitrile; at 80 ℃; for 6h; Inert atmosphere;

DOI:10.1016/j.tet.2016.09.068

Reference yield:

4-benzyloxy-3-methoxyacetophenone (1835-11-6) → 5-(2-(methoxycarbonyl)trans-ethenyl)-7-methoxy-2-(3'-methoxy-4'-(benzyloxy)phenyl)benzofuran (144735-55-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 63 percent / POCl₃ / 1) 0 deg C, 20 min, 2) 65 deg C, 10 h

2: 79 percent / NaOH / H₂O; dioxane / 2 h / 80 °C

3: 1) CuSO₄*H₂O, NH₄OH, NH₂OH*HCl, 2) pyridine / 1) THF, EtOH, 2) 115 deg C, 20 h

With pyridine; ammonium hydroxide; sodium hydroxide; hydroxylamine hydrochloride; copper(II) sulfate; trichlorophosphate; In 1,4-dioxane; water;

DOI:10.1021/jo00052a046

upstream raw materials:

methyl 3-methoxy-4-hydroxy-5-bromocinnamate

1-ethynyl-4-(benzyloxy)-3-methoxybenzene

methyl 3-methoxy-4-hydroxy-5-bromo-cinnamate

cuprous (4-benzyloxy-3-methoxy)phenyl acetylide

Downstream raw materials:

3-nitro-5-(3-acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-(benzyloxy)phenyl)benzofuran

4-acetyl-5-(3-acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-acetoxyphenyl)benzofuran

3-cyano-5-(3-acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-acetoxyphenyl)benzofuran

5-(acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-acetoxyphenyl)benzofuran-3-carbaldehyde