trans-3-[3-(benzofuran-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide

Base Information

• Chemical Name: trans-3-[3-(benzofuran-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide
• CAS No.: 951656-16-9
• Molecular Formula: C₂₃H₂₁NO₅
• Molecular Weight: 391.423
• Mol file: 951656-16-9.mol

Synonyms:trans-3-[3-(benzofuran-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide

Chemical Property of trans-3-[3-(benzofuran-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-3-[3-(benzofuran-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide

There total 5 articles about trans-3-[3-(benzofuran-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide 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: 69.0%

trans-3-[3-(benzofuran-2-carbonyl)phenyl]acrylic acid (951656-14-7) + O-2-tetrahydro-2H-pyranhydroxylamine (6723-30-4) → trans-3-[3-(benzofuran-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide (951656-16-9)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1021/jm0703136

Reference yield:

3-(2-bromoacetyl)benzaldehyde (951656-08-9) → trans-3-[3-(benzofuran-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide (951656-16-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 49 percent / K₂CO₃ / acetonitrile / Heating

2: 40 percent / aq. NaOH; NEt₃ / CH₂Cl₂ / 1 h / 20 °C

3: 95 percent / TFA / 1 h / 20 °C

4: 69 percent / BOP; NEt₃ / dimethylformamide / 1 h / 20 °C

With sodium hydroxide; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2: Wittig olefination;

DOI:10.1021/jm0703136

Reference yield:

3-(benzofuran-2-carbonyl)benzaldehyde (951656-10-3) → trans-3-[3-(benzofuran-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide (951656-16-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 40 percent / aq. NaOH; NEt₃ / CH₂Cl₂ / 1 h / 20 °C

2: 95 percent / TFA / 1 h / 20 °C

3: 69 percent / BOP; NEt₃ / dimethylformamide / 1 h / 20 °C

With sodium hydroxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; 1: Wittig olefination;

DOI:10.1021/jm0703136

upstream raw materials:

trans-3-[3-(benzofuran-2-carbonyl)phenyl]acrylic acid

O-2-tetrahydro-2H-pyranhydroxylamine

3-(2-bromoacetyl)benzaldehyde

3-(benzofuran-2-carbonyl)benzaldehyde

Refernces