Propanedioic acid, 2-(4E)-4-hexen-2-yn-1-yl-2-[(1Z,3E)-4-phenyl-2-[[tris(1-methylethyl)silyl] oxy]-1,3-butadien-1-yl]-, 1,3-dimethyl ester

Base Information

• Chemical Name: Propanedioic acid, 2-(4E)-4-hexen-2-yn-1-yl-2-[(1Z,3E)-4-phenyl-2-[[tris(1-methylethyl)silyl] oxy]-1,3-butadien-1-yl]-, 1,3-dimethyl ester
• CAS No.: 923987-51-3
• Molecular Formula: C30H42O5Si
• Molecular Weight: 510.746
• Mol file: 923987-51-3.mol

Synonyms:

Chemical Property of Propanedioic acid, 2-(4E)-4-hexen-2-yn-1-yl-2-[(1Z,3E)-4-phenyl-2-[[tris(1-methylethyl)silyl] oxy]-1,3-butadien-1-yl]-, 1,3-dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Propanedioic acid, 2-(4E)-4-hexen-2-yn-1-yl-2-[(1Z,3E)-4-phenyl-2-[[tris(1-methylethyl)silyl] oxy]-1,3-butadien-1-yl]-, 1,3-dimethyl ester

There total 4 articles about Propanedioic acid, 2-(4E)-4-hexen-2-yn-1-yl-2-[(1Z,3E)-4-phenyl-2-[[tris(1-methylethyl)silyl] oxy]-1,3-butadien-1-yl]-, 1,3-dimethyl 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: 87.0%

dimethyl [(1Z,3E)-4-phenyl-2-(triisopropylsiloxy)buta-1,3-dienyl](prop-2-ynyl)malonate (923987-63-7) + trans-2-propenyl bromide (590-15-8) → dimethyl [(4E)-hex-4-en-2-ynyl][(1Z,3E)-4-phenyl-2-(triisopropylsiloxy)buta-1,3-dienyl]malonate (923987-51-3)

Guidance literature:

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

DOI:10.1021/ja0671924

Reference yield:

dimethyl [(3E)-2-oxo-4-phenylbut-3-en-1-yl](prop-2-ynyl)malonate (923987-59-1) → dimethyl [(4E)-hex-4-en-2-ynyl][(1Z,3E)-4-phenyl-2-(triisopropylsiloxy)buta-1,3-dienyl]malonate (923987-51-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / Et₃N / CH₂Cl₂ / 20 °C

2: 87 percent / CuI; Pd(PPh₃)4; triethylamine / dimethylformamide / 20 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja0671924

Reference yield:

{(1E)-3-[(trimethylsilyl)oxy]buta-1,3-dien-1-yl}benzene (73400-25-6,124306-12-3,61140-47-4) → dimethyl [(4E)-hex-4-en-2-ynyl][(1Z,3E)-4-phenyl-2-(triisopropylsiloxy)buta-1,3-dienyl]malonate (923987-51-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-bromosuccinimide / tetrahydrofuran / -40 °C

2.1: NaH / tetrahydrofuran / 1.67 h / 0 °C

2.2: 59 percent / tetrahydrofuran

3.1: 68 percent / Et₃N / CH₂Cl₂ / 20 °C

4.1: 87 percent / CuI; Pd(PPh₃)4; triethylamine / dimethylformamide / 20 °C

With N-Bromosuccinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja0671924

upstream raw materials:

dimethyl [(1Z,3E)-4-phenyl-2-(triisopropylsiloxy)buta-1,3-dienyl](prop-2-ynyl)malonate

trans-2-propenyl bromide

dimethyl [(3E)-2-oxo-4-phenylbut-3-en-1-yl](prop-2-ynyl)malonate

(E)-1-bromo-4-phenylbut-3-en-2-one