2,2,2-trichloroethyl (Z)-3-{3,4,5-trimethoxy-2-[2-(trifluoroacetylamino)ethyl]phenyl}prop-2-enyl carbonate

Base Information

• Chemical Name: 2,2,2-trichloroethyl (Z)-3-{3,4,5-trimethoxy-2-[2-(trifluoroacetylamino)ethyl]phenyl}prop-2-enyl carbonate
• CAS No.: 1332523-85-9
• Molecular Formula: C₁₉H₂₁Cl₃F₃NO₇
• Molecular Weight: 538.732

Synonyms:2,2,2-trichloroethyl (Z)-3-{3,4,5-trimethoxy-2-[2-(trifluoroacetylamino)ethyl]phenyl}prop-2-enyl carbonate

Chemical Property of 2,2,2-trichloroethyl (Z)-3-{3,4,5-trimethoxy-2-[2-(trifluoroacetylamino)ethyl]phenyl}prop-2-enyl carbonate

Chemical Property:

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Technology Process of 2,2,2-trichloroethyl (Z)-3-{3,4,5-trimethoxy-2-[2-(trifluoroacetylamino)ethyl]phenyl}prop-2-enyl carbonate

There total 8 articles about 2,2,2-trichloroethyl (Z)-3-{3,4,5-trimethoxy-2-[2-(trifluoroacetylamino)ethyl]phenyl}prop-2-enyl carbonate 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: 71.0%

(Z)-3-{3,4,5-trimethoxy-2-[2-(trifluoroacetylamino)ethyl]-phenyl}prop-2-enol (1332523-83-7) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → 2,2,2-trichloroethyl (Z)-3-{3,4,5-trimethoxy-2-[2-(trifluoroacetylamino)ethyl]phenyl}prop-2-enyl carbonate (1332523-85-9)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tet.2011.05.125

Reference yield:

N-[2-(2,3,4-trimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide (1332523-79-1) → 2,2,2-trichloroethyl (Z)-3-{3,4,5-trimethoxy-2-[2-(trifluoroacetylamino)ethyl]phenyl}prop-2-enyl carbonate (1332523-85-9)

Guidance literature:

Multi-step reaction with 5 steps

1: N-Bromosuccinimide / tetrachloromethane / 16 h / 60 °C / Inert atmosphere

2: N-iodo-succinimide; trifluoroacetic acid / acetonitrile / 24 h / Inert atmosphere; Reflux

3: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diethylamine / 18 h / Inert atmosphere; Reflux

4: sodium tetrahydroborate; hydrogen; nickel diacetate; ethylenediamine / ethanol / 40 h / 20 °C / 760.05 Torr

5: pyridine / dichloromethane / 3 h / 0 °C / Inert atmosphere

With pyridine; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; N-Bromosuccinimide; N-iodo-succinimide; copper(l) iodide; hydrogen; nickel diacetate; ethylenediamine; diethylamine; trifluoroacetic acid; In tetrachloromethane; ethanol; dichloromethane; acetonitrile; 3: Sonogashira coupling;

DOI:10.1016/j.tet.2011.05.125

Reference yield:

N-[2-(5-bromo-2,3,4-trimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide (1332523-80-4) → 2,2,2-trichloroethyl (Z)-3-{3,4,5-trimethoxy-2-[2-(trifluoroacetylamino)ethyl]phenyl}prop-2-enyl carbonate (1332523-85-9)

Guidance literature:

Multi-step reaction with 4 steps

1: N-iodo-succinimide; trifluoroacetic acid / acetonitrile / 24 h / Inert atmosphere; Reflux

2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diethylamine / 18 h / Inert atmosphere; Reflux

3: sodium tetrahydroborate; hydrogen; nickel diacetate; ethylenediamine / ethanol / 40 h / 20 °C / 760.05 Torr

4: pyridine / dichloromethane / 3 h / 0 °C / Inert atmosphere

With pyridine; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; N-iodo-succinimide; copper(l) iodide; hydrogen; nickel diacetate; ethylenediamine; diethylamine; trifluoroacetic acid; In ethanol; dichloromethane; acetonitrile; 2: Sonogashira coupling;

DOI:10.1016/j.tet.2011.05.125

upstream raw materials:

N-[2-(2,3,4-trimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide

N-[2-(5-bromo-2,3,4-trimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide

N-[2-(5-bromo-6-iodo-2,3,4-trimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide

3-{2-bromo-3,4,5-trimethoxy-6-[2-(trifluoroacetylamino)-ethyl]phenyl}prop-2-ynol

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