5-(2-(methoxycarbonyl)-trans-ethenyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde

Base Information

• Chemical Name: 5-(2-(methoxycarbonyl)-trans-ethenyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde
• CAS No.: 144735-63-7
• Molecular Formula: C₂₁H₁₈O₇
• Molecular Weight: 382.37

Synonyms:5-(2-(methoxycarbonyl)-trans-ethenyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde

Chemical Property of 5-(2-(methoxycarbonyl)-trans-ethenyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde

Chemical Property:

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Technology Process of 5-(2-(methoxycarbonyl)-trans-ethenyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde

There total 5 articles about 5-(2-(methoxycarbonyl)-trans-ethenyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde 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)-trans-ethenyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde (144735-63-7)

Guidance literature:

Multi-step reaction with 4 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: 1) KCl, HCl(g) / 1) Et₂O, 0 deg C, 2) EtOH, H₂O, 50 deg C

With pyrrolidine; pyridine; hydrogenchloride; ammonium hydroxide; potassium chloride; hydroxylamine hydrochloride; bromine; copper(II) sulfate; acetic acid; In pyridine;

DOI:10.1021/jo00052a046

Reference yield:

4-benzyloxy-3-methoxyacetophenone (1835-11-6) → 5-(2-(methoxycarbonyl)-trans-ethenyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde (144735-63-7)

Guidance literature:

Multi-step reaction with 4 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: 1) KCl, HCl(g) / 1) Et₂O, 0 deg C, 2) EtOH, H₂O, 50 deg C

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

DOI:10.1021/jo00052a046

Reference yield:

β-(3-methoxy-4-(benzyloxy)phenyl)-β-chloracrolein (144735-53-5) → 5-(2-(methoxycarbonyl)-trans-ethenyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde (144735-63-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / NaOH / H₂O; dioxane / 2 h / 80 °C

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

3: 1) KCl, HCl(g) / 1) Et₂O, 0 deg C, 2) EtOH, H₂O, 50 deg C

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

DOI:10.1021/jo00052a046

upstream raw materials:

dicyanozinc

5-(2-(methoxycarbonyl)trans-ethenyl)-7-methoxy-2-(3'-methoxy-4'-(benzyloxy)phenyl)benzofuran

vanillin

4-benzyloxy-3-methoxyacetophenone

Downstream raw materials:

5-(2-carboxy-trans-ethenyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde

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