dimethyl 2-(but-2-yn-1-yl)-2-(3-oxo-3-phenylpropyl)malonate

Base Information

• Chemical Name: dimethyl 2-(but-2-yn-1-yl)-2-(3-oxo-3-phenylpropyl)malonate
• CAS No.: 1357173-35-3
• Molecular Formula: C₁₈H₂₀O₅
• Molecular Weight: 316.354
• Mol file: 1357173-35-3.mol

Synonyms:dimethyl 2-(but-2-yn-1-yl)-2-(3-oxo-3-phenylpropyl)malonate

Chemical Property of dimethyl 2-(but-2-yn-1-yl)-2-(3-oxo-3-phenylpropyl)malonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of dimethyl 2-(but-2-yn-1-yl)-2-(3-oxo-3-phenylpropyl)malonate

There total 2 articles about dimethyl 2-(but-2-yn-1-yl)-2-(3-oxo-3-phenylpropyl)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:

malonic acid dimethyl ester (108-59-8) → dimethyl 2-(but-2-yn-1-yl)-2-(3-oxo-3-phenylpropyl)malonate (1357173-35-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 °C

2.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 °C

2.2: Reflux

With sodium hydride; In tetrahydrofuran; mineral oil;

DOI:10.1039/d1cc06379k

Reference yield:

(Z)-dimethyl 2-(but-2-ynyl)-2-(3-phenyl-3-(triisopropylsilyloxy)allyl)malonate (1357172-64-5) → dimethyl 2-(but-2-yn-1-yl)-2-(3-oxo-3-phenylpropyl)malonate (1357173-35-3) + C18H20O5

Guidance literature:

With C₁₉H₂₀AuClN₂S; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; In 1,2-dichloro-ethane; at -30 ℃; for 16h; Overall yield = 17 %;

DOI:10.1002/chem.201804653

Reference yield: 76.0%

dimethyl 2-(but-2-yn-1-yl)-2-(3-oxo-3-phenylpropyl)malonate (1357173-35-3) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (Z)-dimethyl 2-(but-2-ynyl)-2-(3-phenyl-3-(triisopropylsilyloxy)allyl)malonate (1357172-64-5)

Guidance literature:

dimethyl 2-(but-2-yn-1-yl)-2-(3-oxo-3-phenylpropyl)malonate; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

triisopropylsilyl trifluoromethanesulfonate; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/ja210388g

upstream raw materials:

(Z)-dimethyl 2-(but-2-ynyl)-2-(3-phenyl-3-(triisopropylsilyloxy)allyl)malonate

malonic acid dimethyl ester

Downstream raw materials:

(Z)-dimethyl 3-benzoyl-4-ethylidenecyclopentane-1,1-dicarboxylate

(Z)-dimethyl 2-(but-2-ynyl)-2-(3-phenyl-3-(triisopropylsilyloxy)allyl)malonate