Benzofuran, 2,3-dihydro-2-[2-(4-methoxyphenyl)ethenyl]-3,3-dimethyl-5-(phenylmeth oxy)-

Base Information

• Chemical Name: Benzofuran, 2,3-dihydro-2-[2-(4-methoxyphenyl)ethenyl]-3,3-dimethyl-5-(phenylmeth oxy)-
• CAS No.: 138854-03-2
• Molecular Formula: C26H26O3
• Molecular Weight: 386.491
• Mol file: 138854-03-2.mol

Synonyms:

Chemical Property of Benzofuran, 2,3-dihydro-2-[2-(4-methoxyphenyl)ethenyl]-3,3-dimethyl-5-(phenylmeth oxy)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzofuran, 2,3-dihydro-2-[2-(4-methoxyphenyl)ethenyl]-3,3-dimethyl-5-(phenylmeth oxy)-

There total 7 articles about Benzofuran, 2,3-dihydro-2-[2-(4-methoxyphenyl)ethenyl]-3,3-dimethyl-5-(phenylmeth oxy)- 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:

1-methoxy-4-(3-methylbut-2-enyloxy)-benzene (34125-69-4) → 5-(benzyloxy)-2,3-dihydro-3,3-dimethyl-2-<2-(4-methoxyphenyl)ethenyl>benzofuran (138854-03-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) N,N-dimethylaniline, 2.) m-chloroperbenzoic acid / 1.) 1,2-dichlorobenzene, reflux, 24 h, 2.) 1,2-dichlorobenzene, dichloromethane, RT, overnight

2: 98 percent / NaOEt / ethanol / 0.5 h / 5 °C

3: 47 percent / BBr₃ / CH₂Cl₂ / -78 °C

4: 71 percent / K₂CO₃ / butan-2-one / 18 h / Heating

5: 1.) oxalyl chloride, DMSO / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -78 deg C, 30 min

6: 1.) hexamethyldisialzide / 1.) THF, -78 deg C, 30 min, 2.) THF, 0 deg C, 30 min

With oxalyl dichloride; sodium ethanolate; boron tribromide; potassium carbonate; dimethyl sulfoxide; N,N-dimethyl-aniline; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In ethanol; dichloromethane; butanone;

DOI:10.1021/jm00085a019

Reference yield:

4-methoxy-phenol (150-76-5) → 5-(benzyloxy)-2,3-dihydro-3,3-dimethyl-2-<2-(4-methoxyphenyl)ethenyl>benzofuran (138854-03-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 70 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 1 h / Ambient temperature

2: 1.) N,N-dimethylaniline, 2.) m-chloroperbenzoic acid / 1.) 1,2-dichlorobenzene, reflux, 24 h, 2.) 1,2-dichlorobenzene, dichloromethane, RT, overnight

3: 98 percent / NaOEt / ethanol / 0.5 h / 5 °C

4: 47 percent / BBr₃ / CH₂Cl₂ / -78 °C

5: 71 percent / K₂CO₃ / butan-2-one / 18 h / Heating

6: 1.) oxalyl chloride, DMSO / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -78 deg C, 30 min

7: 1.) hexamethyldisialzide / 1.) THF, -78 deg C, 30 min, 2.) THF, 0 deg C, 30 min

With oxalyl dichloride; sodium ethanolate; boron tribromide; potassium carbonate; dimethyl sulfoxide; N,N-dimethyl-aniline; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; butanone;

DOI:10.1021/jm00085a019

Reference yield:

2,3-dihydro-3,3-dimethyl-2-(hydroxymethyl)-5-benzofuranol (138854-50-9) → 5-(benzyloxy)-2,3-dihydro-3,3-dimethyl-2-<2-(4-methoxyphenyl)ethenyl>benzofuran (138854-03-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 71 percent / K₂CO₃ / butan-2-one / 18 h / Heating

2: 1.) oxalyl chloride, DMSO / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -78 deg C, 30 min

3: 1.) hexamethyldisialzide / 1.) THF, -78 deg C, 30 min, 2.) THF, 0 deg C, 30 min

With oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; 1,1,1,3,3,3-hexamethyl-disilazane; In butanone;

DOI:10.1021/jm00085a019

upstream raw materials:

diethyl 4-methoxybenzylphosphonate

5-(benzyloxy)-2,3-dihydro-3,3-dimethylbenzofuran-2-carboxaldehyde

1-methoxy-4-(3-methylbut-2-enyloxy)-benzene

4-methoxy-phenol

Downstream raw materials:

6-allyl-2,3-dihydro-3,3-dimethyl-2-<2-(4-methoxyphenyl)ethyl>-5-benzofuranol

5-(allyloxy)-2,3-dihydro-3,3-dimethyl-2-<2-(4-methoxyphenyl)ethyl>benzofuran