N-[3-formyl-5-methyl-2-(trimethylsilylethynyl)phenyl]acetamide

Base Information

• Chemical Name: N-[3-formyl-5-methyl-2-(trimethylsilylethynyl)phenyl]acetamide
• CAS No.: 868050-20-8
• Molecular Formula: C₁₅H₁₉NO₂Si
• Molecular Weight: 273.407
• Mol file: 868050-20-8.mol

Synonyms:N-[3-formyl-5-methyl-2-(trimethylsilylethynyl)phenyl]acetamide

Chemical Property of N-[3-formyl-5-methyl-2-(trimethylsilylethynyl)phenyl]acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[3-formyl-5-methyl-2-(trimethylsilylethynyl)phenyl]acetamide

There total 3 articles about N-[3-formyl-5-methyl-2-(trimethylsilylethynyl)phenyl]acetamide 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: 80.0%

2-acetylamino-6-formyl-4-methylphenyl trifluoromethanesulfonate (868050-16-2) + trimethylsilylacetylene (1066-54-2) → N-[3-formyl-5-methyl-2-(trimethylsilylethynyl)phenyl]acetamide (868050-20-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; at 55 ℃; for 5h;

DOI:10.1016/j.tet.2005.08.004

Reference yield:

N-(3-formyl-2-hydroxy-5-methyl-phenyl)-acetamide (868050-23-1) → N-[3-formyl-5-methyl-2-(trimethylsilylethynyl)phenyl]acetamide (868050-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / K₂CO₃ / tetrahydrofuran / 20 °C

2: 80 percent / diisopropylethylamine / PdCl₂(PPh₃)2; CuI / tetrahydrofuran / 5 h / 55 °C

With potassium carbonate; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; 2: Sonogashira coupling;

DOI:10.1016/j.tet.2005.08.004

Reference yield:

2-hydroxy-5-methyl-3-nitro-benzaldehyde (66620-31-3) → N-[3-formyl-5-methyl-2-(trimethylsilylethynyl)phenyl]acetamide (868050-20-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / H₂ / Pd/C / ethyl acetate / 20 °C

2: 95 percent / K₂CO₃ / tetrahydrofuran / 20 °C

3: 80 percent / diisopropylethylamine / PdCl₂(PPh₃)2; CuI / tetrahydrofuran / 5 h / 55 °C

With hydrogen; potassium carbonate; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; palladium on activated charcoal; copper(l) iodide; In tetrahydrofuran; ethyl acetate; 3: Sonogashira coupling;

DOI:10.1016/j.tet.2005.08.004

upstream raw materials:

2-acetylamino-6-formyl-4-methylphenyl trifluoromethanesulfonate

trimethylsilylacetylene

N-(3-formyl-2-hydroxy-5-methyl-phenyl)-acetamide

2-hydroxy-5-methyl-3-nitro-benzaldehyde

Downstream raw materials:

6-methylindole-4-carboxaldehyde