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

Base Information

• Chemical Name: dimethyl [(4Z)-hex-4-en-2-ynyl][(1Z,3E)-4-phenyl-2-(triisopropylsiloxy)buta-1,3-dienyl]malonate
• CAS No.: 923987-67-1
• Molecular Formula: C₃₀H₄₂O₅Si
• Molecular Weight: 510.746
• Mol file: 923987-67-1.mol

Synonyms:dimethyl [(4Z)-hex-4-en-2-ynyl][(1Z,3E)-4-phenyl-2-(triisopropylsiloxy)buta-1,3-dienyl]malonate

Chemical Property of dimethyl [(4Z)-hex-4-en-2-ynyl][(1Z,3E)-4-phenyl-2-(triisopropylsiloxy)buta-1,3-dienyl]malonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl [(4Z)-hex-4-en-2-ynyl][(1Z,3E)-4-phenyl-2-(triisopropylsiloxy)buta-1,3-dienyl]malonate

There total 4 articles about dimethyl [(4Z)-hex-4-en-2-ynyl][(1Z,3E)-4-phenyl-2-(triisopropylsiloxy)buta-1,3-dienyl]malonate 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: 75.0%

dimethyl [(1Z,3E)-4-phenyl-2-(triisopropylsiloxy)buta-1,3-dienyl](prop-2-ynyl)malonate (923987-63-7) + (Z)-1-propenyl bromide (590-13-6) → dimethyl [(4Z)-hex-4-en-2-ynyl][(1Z,3E)-4-phenyl-2-(triisopropylsiloxy)buta-1,3-dienyl]malonate (923987-67-1)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine; piperidine; at 60 ℃; for 3h;

DOI:10.1021/ja0671924

Reference yield:

dimethyl [(3E)-2-oxo-4-phenylbut-3-en-1-yl](prop-2-ynyl)malonate (923987-59-1) → dimethyl [(4Z)-hex-4-en-2-ynyl][(1Z,3E)-4-phenyl-2-(triisopropylsiloxy)buta-1,3-dienyl]malonate (923987-67-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / Et₃N / CH₂Cl₂ / 20 °C

2: 75 percent / CuI; PPh₃; Pd(PPh₃)4 / piperidine / 3 h / 60 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; triphenylphosphine; piperidine; In dichloromethane;

DOI:10.1021/ja0671924

Reference yield:

(E)-1-bromo-4-phenylbut-3-en-2-one (22422-16-8,55650-14-1) → dimethyl [(4Z)-hex-4-en-2-ynyl][(1Z,3E)-4-phenyl-2-(triisopropylsiloxy)buta-1,3-dienyl]malonate (923987-67-1)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 59 percent / tetrahydrofuran

2.1: 68 percent / Et₃N / CH₂Cl₂ / 20 °C

3.1: 75 percent / CuI; PPh₃; Pd(PPh₃)4 / piperidine / 3 h / 60 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; triethylamine; triphenylphosphine; piperidine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja0671924

upstream raw materials:

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

(Z)-1-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