5-Benzofuranpropanoic acid, a-(ethylthio)-2-[(5-methyl-2-phenyl-4-oxazolyl)methyl]-, ethyl ester

Base Information

• Chemical Name: 5-Benzofuranpropanoic acid, a-(ethylthio)-2-[(5-methyl-2-phenyl-4-oxazolyl)methyl]-, ethyl ester
• CAS No.: 140129-51-7
• Molecular Formula: C26H27NO4S
• Molecular Weight: 449.571
• Mol file: 140129-51-7.mol

Synonyms:

Chemical Property of 5-Benzofuranpropanoic acid, a-(ethylthio)-2-[(5-methyl-2-phenyl-4-oxazolyl)methyl]-, ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Benzofuranpropanoic acid, a-(ethylthio)-2-[(5-methyl-2-phenyl-4-oxazolyl)methyl]-, ethyl ester

There total 8 articles about 5-Benzofuranpropanoic acid, a-(ethylthio)-2-[(5-methyl-2-phenyl-4-oxazolyl)methyl]-, ethyl ester 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:

4-bromoacetyl-5-methyl-2-phenyl-oxazole (103788-62-1) → Ethyl 2-ethylthio-3-[2-((5-methyl-2-phenyl-4-oxazolyl)methyl)benzofuran-5-yl]propanoate (140129-51-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / diisopropylethylamine / dimethylformamide / 3 h / 91 - 94 °C

2: 100 percent / NaBH₄ / methanol; tetrahydrofuran / 2 h / 0 °C

3: 95 percent / Et₃SiH, TFA / 1.) 0 deg C, 1.5 h, 2.) RT, overnight

4: 80 percent / H₂ / PtO₂ / ethyl acetate / 1.25 h / 2068.6 Torr

5: 1.) 48percent aq. HBr, sodium nitrite, 2.) Cu₂O / 1.) acetone, methanol, from 0 to 5 deg C, 15 min, 2.) acetone, methanol, 1 h

6: K₂CO₃ / dimethylformamide / Ambient temperature

With copper(I) oxide; triethylsilane; sodium tetrahydroborate; hydrogen bromide; hydrogen; potassium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium nitrite; platinum(IV) oxide; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm960230h

Reference yield:

5-Nitrosalicylaldehyde (97-51-8) → Ethyl 2-ethylthio-3-[2-((5-methyl-2-phenyl-4-oxazolyl)methyl)benzofuran-5-yl]propanoate (140129-51-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / diisopropylethylamine / dimethylformamide / 3 h / 91 - 94 °C

2: 100 percent / NaBH₄ / methanol; tetrahydrofuran / 2 h / 0 °C

3: 95 percent / Et₃SiH, TFA / 1.) 0 deg C, 1.5 h, 2.) RT, overnight

4: 80 percent / H₂ / PtO₂ / ethyl acetate / 1.25 h / 2068.6 Torr

5: 1.) 48percent aq. HBr, sodium nitrite, 2.) Cu₂O / 1.) acetone, methanol, from 0 to 5 deg C, 15 min, 2.) acetone, methanol, 1 h

6: K₂CO₃ / dimethylformamide / Ambient temperature

With copper(I) oxide; triethylsilane; sodium tetrahydroborate; hydrogen bromide; hydrogen; potassium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium nitrite; platinum(IV) oxide; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm960230h

Reference yield:

5-Methyl-4-(5-nitro-benzofuran-2-ylmethyl)-2-phenyl-oxazole (140129-99-3) → Ethyl 2-ethylthio-3-[2-((5-methyl-2-phenyl-4-oxazolyl)methyl)benzofuran-5-yl]propanoate (140129-51-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / H₂ / PtO₂ / ethyl acetate / 1.25 h / 2068.6 Torr

2: 1.) 48percent aq. HBr, sodium nitrite, 2.) Cu₂O / 1.) acetone, methanol, from 0 to 5 deg C, 15 min, 2.) acetone, methanol, 1 h

3: K₂CO₃ / dimethylformamide / Ambient temperature

With copper(I) oxide; hydrogen bromide; hydrogen; potassium carbonate; sodium nitrite; platinum(IV) oxide; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm960230h

upstream raw materials:

ethyl alpha-bromo-2-(5-methyl-2-phenyl-4-oxazolyl)methyl-5-benzofuranpropanoic acid

ethanethiol

4-bromoacetyl-5-methyl-2-phenyl-oxazole

5-Nitrosalicylaldehyde