methyl 2-[3-(methoxycarbonyl)-4-(2-thienylethynyl)phenylethynyl]-5-(trimethylsilylethynyl)benzoate

Base Information

Chemical Name:methyl 2-[3-(methoxycarbonyl)-4-(2-thienylethynyl)phenylethynyl]-5-(trimethylsilylethynyl)benzoate
CAS No.:879413-42-0
Molecular Formula:C₂₉H₂₄O₄SSi
Molecular Weight:496.659
Hs Code.:

Synonyms:methyl 2-[3-(methoxycarbonyl)-4-(2-thienylethynyl)phenylethynyl]-5-(trimethylsilylethynyl)benzoate

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Chemical Property of methyl 2-[3-(methoxycarbonyl)-4-(2-thienylethynyl)phenylethynyl]-5-(trimethylsilylethynyl)benzoate

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Technology Process of methyl 2-[3-(methoxycarbonyl)-4-(2-thienylethynyl)phenylethynyl]-5-(trimethylsilylethynyl)benzoate

There total 4 articles about methyl 2-[3-(methoxycarbonyl)-4-(2-thienylethynyl)phenylethynyl]-5-(trimethylsilylethynyl)benzoate 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: 61.0%

: 879413-33-9
methyl 5-ethynyl-2-(2-thienylethynyl)benzoate

: 251564-53-1
methyl 2-iodo-5-(trimethylsilylethynyl)benzoate

: 879413-42-0
methyl 2-[3-(methoxycarbonyl)-4-(2-thienylethynyl)phenylethynyl]-5-(trimethylsilylethynyl)benzoate

Guidance literature:: With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 20 ℃; for 18h;
DOI:10.1016/j.tet.2005.11.015

Reference yield:

: 119754-20-0
methyl 5-(trimethylsilylethynyl)anthranilate

: 879413-42-0
methyl 2-[3-(methoxycarbonyl)-4-(2-thienylethynyl)phenylethynyl]-5-(trimethylsilylethynyl)benzoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: BF₃*OEt₂; tert-butyl nitrite / diethyl ether / 0.75 h / -20 - 0 °C

1.2: 74 percent / NaI; I₂ / acetonitrile / 1 h / 20 °C

2.1: 80 percent / triethylamine; CuI / Pd(PPh₃)2Cl₂ / dimethylformamide / 18 h / 20 °C

3.1: 97 percent / anhydrous potassium carbonate / methanol; CH₂Cl₂ / 3 h / 20 °C

4.1: 61 percent / triethylamine; CuI / Pd(PPh₃)2Cl₂ / dimethylformamide / 18 h / 20 °C

With copper(l) iodide; tert.-butylnitrite; boron trifluoride diethyl etherate; potassium carbonate; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 2.1: Sonogashira coupling / 4.1: Sonogashira coupling;
DOI:10.1016/j.tet.2005.11.015

Reference yield:

: 879413-23-7
methyl 2-(2-thienylethynyl)-5-(trimethylsilylethynyl)benzoate

: 879413-42-0
methyl 2-[3-(methoxycarbonyl)-4-(2-thienylethynyl)phenylethynyl]-5-(trimethylsilylethynyl)benzoate

Guidance literature:: Multi-step reaction with 2 steps

1: 97 percent / anhydrous potassium carbonate / methanol; CH₂Cl₂ / 3 h / 20 °C

2: 61 percent / triethylamine; CuI / Pd(PPh₃)2Cl₂ / dimethylformamide / 18 h / 20 °C

With copper(l) iodide; potassium carbonate; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In methanol; dichloromethane; N,N-dimethyl-formamide; 2: Sonogashira coupling;
DOI:10.1016/j.tet.2005.11.015