{5-methoxy-2-[(trimethylsilyl)ethynyl]phenyl}carbamic acid 1,1-dimethylethyl ester

Base Information

• Chemical Name: {5-methoxy-2-[(trimethylsilyl)ethynyl]phenyl}carbamic acid 1,1-dimethylethyl ester
• CAS No.: 1038778-97-0
• Molecular Formula: C₁₇H₂₅NO₃Si
• Molecular Weight: 319.476
• Mol file: 1038778-97-0.mol

Synonyms:{5-methoxy-2-[(trimethylsilyl)ethynyl]phenyl}carbamic acid 1,1-dimethylethyl ester

Chemical Property of {5-methoxy-2-[(trimethylsilyl)ethynyl]phenyl}carbamic acid 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {5-methoxy-2-[(trimethylsilyl)ethynyl]phenyl}carbamic acid 1,1-dimethylethyl ester

There total 2 articles about {5-methoxy-2-[(trimethylsilyl)ethynyl]phenyl}carbamic acid 1,1-dimethylethyl 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: 80.0%

(2-iodo-5-methoxyphenyl)carbamic acid 1,1-dimethylethyl ester (1038778-89-0) + trimethylsilylacetylene (1066-54-2) → {5-methoxy-2-[(trimethylsilyl)ethynyl]phenyl}carbamic acid 1,1-dimethylethyl ester (1038778-97-0)

Guidance literature:

With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; at 20 ℃; for 24h;

DOI:10.1016/j.tet.2008.03.025

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → {5-methoxy-2-[(trimethylsilyl)ethynyl]phenyl}carbamic acid 1,1-dimethylethyl ester (1038778-97-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

1.2: 0.75 h / 0 - 20 °C / Inert atmosphere

2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; sodium hexamethyldisilazane; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; 2.1: |Sonogashira Cross-Coupling;

DOI:10.1021/acs.orglett.6b00390

Reference yield: 70.0%

{5-methoxy-2-[(trimethylsilyl)ethynyl]phenyl}carbamic acid 1,1-dimethylethyl ester (1038778-97-0) → (2-ethynyl-5-methoxyphenyl)carbamic acid 1,1-dimethylethyl ester (1038779-07-5)

Guidance literature:

With potassium fluoride; water; In tetrahydrofuran; methanol; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2008.03.025

upstream raw materials:

(2-iodo-5-methoxyphenyl)carbamic acid 1,1-dimethylethyl ester

trimethylsilylacetylene

di-tert-butyl dicarbonate

Downstream raw materials:

(2-ethynyl-5-methoxyphenyl)carbamic acid 1,1-dimethylethyl ester