Methyl 3-formyl-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-benzofuranpropanoate

Base Information

• Chemical Name: Methyl 3-formyl-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-benzofuranpropanoate
• CAS No.: 144735-59-1
• Molecular Formula: C₂₁H₂₀O₇
• Molecular Weight: 384.386
• DSSTox Substance ID: DTXSID901138398

Synonyms:ICCB1_000072;DTXSID901138398;Methyl 3-formyl-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-benzofuranpropanoate;144735-59-1

Chemical Property of Methyl 3-formyl-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-benzofuranpropanoate

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 384.12090297
• Heavy Atom Count: 28
• Complexity: 539

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC(=CC2=C1OC(=C2C=O)C3=CC(=C(C=C3)O)OC)CCC(=O)OC

Technology Process of Methyl 3-formyl-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-benzofuranpropanoate

There total 9 articles about Methyl 3-formyl-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-benzofuranpropanoate 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:

vanillin (121-33-5,8014-42-4) → 5-(2-(methoxycarbonyl)ethyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde (144735-59-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / Br₂, HOAc / 1 h / Ambient temperature

2: 98 percent / pyrrolidine / pyridine / 6 h / 100 °C

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

4: 92 percent / H₂ / 5percent Pd-C / tetrahydrofuran / 10 h / Ambient temperature

5: 1) KCl, HCl(g) / 1) Et₂O, 0 deg C, 2) GH₂O, EtOH, 50 deg C, 30 min

With pyrrolidine; pyridine; hydrogenchloride; ammonium hydroxide; potassium chloride; hydroxylamine hydrochloride; hydrogen; bromine; copper(II) sulfate; acetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine;

DOI:10.1021/jo00052a046

Reference yield:

4-benzyloxy-3-methoxyacetophenone (1835-11-6) → 5-(2-(methoxycarbonyl)ethyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde (144735-59-1)

Guidance literature:

Multi-step reaction with 5 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

4: 92 percent / H₂ / 5percent Pd-C / tetrahydrofuran / 10 h / Ambient temperature

5: 1) KCl, HCl(g) / 1) Et₂O, 0 deg C, 2) GH₂O, EtOH, 50 deg C, 30 min

With pyridine; hydrogenchloride; ammonium hydroxide; sodium hydroxide; potassium chloride; hydroxylamine hydrochloride; hydrogen; copper(II) sulfate; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1021/jo00052a046

Reference yield:

5-bromo-4-hydroxy-3-methoxybenzaldehyde (2973-76-4) → 5-(2-(methoxycarbonyl)ethyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde (144735-59-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / pyrrolidine / pyridine / 6 h / 100 °C

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

3: 92 percent / H₂ / 5percent Pd-C / tetrahydrofuran / 10 h / Ambient temperature

4: 1) KCl, HCl(g) / 1) Et₂O, 0 deg C, 2) GH₂O, EtOH, 50 deg C, 30 min

With pyrrolidine; pyridine; hydrogenchloride; ammonium hydroxide; potassium chloride; hydroxylamine hydrochloride; hydrogen; copper(II) sulfate; palladium on activated charcoal; In tetrahydrofuran; pyridine;

DOI:10.1021/jo00052a046

upstream raw materials:

dicyanozinc

5-((2-methoxycarbonyl)ethyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran

vanillin

4-benzyloxy-3-methoxyacetophenone

Downstream raw materials:

5-(2-carboxyethyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde

5-(2-(methoxycarbonyl)ethyl)-7-methoxy-3-methyl-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran

3-(hydroxymethyl)-5-(2-(methoxycarbonyl)ethyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran

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