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

Base Information

• Chemical Name: 5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-(benzyloxy)phenyl)benzofuran
• CAS No.: 135040-86-7
• Molecular Formula: C₂₆H₂₆O₅
• Molecular Weight: 418.489
• Mol file: 135040-86-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about 5-(3-hydroxypropyl)-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: 90.0%

5-(2-(methoxycarbonyl)trans-ethenyl)-7-methoxy-2-(3'-methoxy-4'-(benzyloxy)phenyl)benzofuran (144735-55-7) → 5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-(benzyloxy)phenyl)benzofuran (135040-86-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran;

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

Reference yield: 55.0%

2-(4-benzyloxy-3-methoxyphenyl)-5-carbethoxyethenyl-3-iodo-7-methoxybenzofuran → 5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-(benzyloxy)phenyl)benzofuran (135040-86-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 - 50 ℃; Inert atmosphere;

DOI:10.5012/bkcs.2010.31.04.965

Reference yield:

vanillin (121-33-5,8014-42-4) → 5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-(benzyloxy)phenyl)benzofuran (135040-86-7)

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: 72 percent / LiAlH₄ / tetrahydrofuran / 4 h / Ambient temperature

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

DOI:10.1021/jo00052a046

upstream raw materials:

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

vanillin

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

benzyl bromide

Downstream raw materials:

2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxybenzofurane

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

2-(4-hydroxy-3-methoxyphenyl)-5-(3-acetoxypropyl)-7-methoxybenzofuran

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

Refernces

• 1、 Yang, Zhen,Liu, Han Biao,Lee, Chi Ming,Chang, Hson Mou,Wong, Henry N. C.. "Regioselective Introduction of Carbon-3 Substituents to 5-Alkyl-7-methoxy-2-phenylbenzofurans: Synthesis of a Novel Adenosine A1 Receptor Ligand and Its Derivatives". . p. 7248 - 7257. Retrieved 2007/10/02.