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

Base Information

• Chemical Name: 3-nitro-5-(3-acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-(benzyloxy)phenyl)benzofuran
• CAS No.: 144735-71-7
• Molecular Formula: C₂₈H₂₇NO₈
• Molecular Weight: 505.524

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

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

Chemical Property:

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

There total 9 articles about 3-nitro-5-(3-acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-(benzyloxy)phenyl)benzofuran 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%

Acetic acid 3-[2-(4-benzyloxy-3-methoxy-phenyl)-7-methoxy-benzofuran-5-yl]-propyl ester (135040-87-8) → 3-nitro-5-(3-acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-(benzyloxy)phenyl)benzofuran (144735-71-7)

Guidance literature:

With nitric acid; acetic acid; 1) 0 deg C, 20 min, 2) RT, 2 h;

DOI:10.1021/jo00052a046

Reference yield:

vanillin (121-33-5,8014-42-4) → 3-nitro-5-(3-acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-(benzyloxy)phenyl)benzofuran (144735-71-7)

Guidance literature:

Multi-step reaction with 6 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: 72 percent / LiAlH₄ / tetrahydrofuran / 4 h / Ambient temperature

5: 80 percent / pyridine / 18 h / Ambient temperature

6: 67 percent / gl. HOAc, HNO₃ / 1) 0 deg C, 20 min, 2) RT, 2 h

With pyrrolidine; pyridine; ammonium hydroxide; lithium aluminium tetrahydride; hydroxylamine hydrochloride; bromine; nitric acid; copper(II) sulfate; acetic acid; In tetrahydrofuran; pyridine;

DOI:10.1021/jo00052a046

Reference yield:

4-benzyloxy-3-methoxyacetophenone (1835-11-6) → 3-nitro-5-(3-acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-(benzyloxy)phenyl)benzofuran (144735-71-7)

Guidance literature:

Multi-step reaction with 6 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: 72 percent / LiAlH₄ / tetrahydrofuran / 4 h / Ambient temperature

5: 80 percent / pyridine / 18 h / Ambient temperature

6: 67 percent / gl. HOAc, HNO₃ / 1) 0 deg C, 20 min, 2) RT, 2 h

With pyridine; ammonium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; hydroxylamine hydrochloride; nitric acid; copper(II) sulfate; acetic acid; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1021/jo00052a046

upstream raw materials:

Acetic acid 3-[2-(4-benzyloxy-3-methoxy-phenyl)-7-methoxy-benzofuran-5-yl]-propyl ester

vanillin

4-benzyloxy-3-methoxyacetophenone

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

Downstream raw materials:

3-nitro-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran

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

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