[3-(3-cyano-4-hydroxyphenyl)-prop-2-ynyl]carbamic acid 2-trimethylsilylethyl ester

Base Information

• Chemical Name: [3-(3-cyano-4-hydroxyphenyl)-prop-2-ynyl]carbamic acid 2-trimethylsilylethyl ester
• CAS No.: 883455-49-0
• Molecular Formula: C₁₆H₂₀N₂O₃Si
• Molecular Weight: 316.432
• Mol file: 883455-49-0.mol

Synonyms:[3-(3-cyano-4-hydroxyphenyl)-prop-2-ynyl]carbamic acid 2-trimethylsilylethyl ester

Chemical Property of [3-(3-cyano-4-hydroxyphenyl)-prop-2-ynyl]carbamic acid 2-trimethylsilylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [3-(3-cyano-4-hydroxyphenyl)-prop-2-ynyl]carbamic acid 2-trimethylsilylethyl ester

There total 3 articles about [3-(3-cyano-4-hydroxyphenyl)-prop-2-ynyl]carbamic acid 2-trimethylsilylethyl 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: 95.0%

2-hydroxy-5-iodobenzonitrile (685103-95-1) + prop-2-ynylcarbamic acid 2-trimethylsilylethyl ester (221101-02-6) → [3-(3-cyano-4-hydroxyphenyl)-prop-2-ynyl]carbamic acid 2-trimethylsilylethyl ester (883455-49-0)

Guidance literature:

With copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1016/j.tet.2005.12.012

Reference yield:

p-nitrophenyl-2-trimethylsilylethyl-carbonate → [3-(3-cyano-4-hydroxyphenyl)-prop-2-ynyl]carbamic acid 2-trimethylsilylethyl ester (883455-49-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / ethyldiisopropylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 48 h / Heating

2: 95 percent / ethyldiisopropylamine; copper(I) iodide / Pd(PPh₃)4 / dimethylformamide / 0 - 20 °C

With dmap; copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; N,N-dimethyl-formamide; 2: Sonogashira coupling;

DOI:10.1016/j.tet.2005.12.012

Reference yield:

salicylonitrile (611-20-1) → [3-(3-cyano-4-hydroxyphenyl)-prop-2-ynyl]carbamic acid 2-trimethylsilylethyl ester (883455-49-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / HBF₄; N-iodosuccinimide / acetonitrile / 4 h / -10 - 20 °C

2: 95 percent / ethyldiisopropylamine; copper(I) iodide / Pd(PPh₃)4 / dimethylformamide / 0 - 20 °C

With N-iodo-succinimide; copper(l) iodide; tetrafluoroboric acid; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; acetonitrile; 2: Sonogashira coupling;

DOI:10.1016/j.tet.2005.12.012

upstream raw materials:

2-hydroxy-5-iodobenzonitrile

prop-2-ynylcarbamic acid 2-trimethylsilylethyl ester

salicylonitrile

Downstream raw materials:

[3-(3-cyano-4-hydroxyphenyl)-propyl]carbamic acid 2-trimethylsilyle 2-trimethylsilylethyl ester