acetic acid 2-[3-(2-formyl-phenyl)-prop-2-ynyl]-2-methyl-3-oxo-1-trimethylsilanylethynylcyclopentyl ester

Base Information

• Chemical Name: acetic acid 2-[3-(2-formyl-phenyl)-prop-2-ynyl]-2-methyl-3-oxo-1-trimethylsilanylethynylcyclopentyl ester
• CAS No.: 911653-40-2
• Molecular Formula: C₂₃H₂₆O₄Si
• Molecular Weight: 394.543
• Mol file: 911653-40-2.mol

Synonyms:acetic acid 2-[3-(2-formyl-phenyl)-prop-2-ynyl]-2-methyl-3-oxo-1-trimethylsilanylethynylcyclopentyl ester

Chemical Property of acetic acid 2-[3-(2-formyl-phenyl)-prop-2-ynyl]-2-methyl-3-oxo-1-trimethylsilanylethynylcyclopentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of acetic acid 2-[3-(2-formyl-phenyl)-prop-2-ynyl]-2-methyl-3-oxo-1-trimethylsilanylethynylcyclopentyl ester

There total 4 articles about acetic acid 2-[3-(2-formyl-phenyl)-prop-2-ynyl]-2-methyl-3-oxo-1-trimethylsilanylethynylcyclopentyl 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: 88.0%

3-acetoxy-2-methyl-2-prop-2-ynyl-3-trimethylsilanylethynyl-cyclopentanone (911651-99-5) + ortho-bromobenzaldehyde (6630-33-7) → acetic acid 2-[3-(2-formyl-phenyl)-prop-2-ynyl]-2-methyl-3-oxo-1-trimethylsilanylethynylcyclopentyl ester (911653-40-2)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 80 ℃; for 7h;

DOI:10.1021/jo060606r

Reference yield:

2-Methylcyclopentane-1,3-dione (765-69-5) → acetic acid 2-[3-(2-formyl-phenyl)-prop-2-ynyl]-2-methyl-3-oxo-1-trimethylsilanylethynylcyclopentyl ester (911653-40-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 80 percent / NaOH / H₂O / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -70 °C

2.2: 84 percent / tetrahydrofuran; hexane / 3 h / -70 °C

3.1: 85 percent / 4-dimethylaminopyridine; Et₃N / 20 h / 20 °C

4.1: 88 percent / PdCl₂(PPh₃)2; CuI; Et₃N / 7 h / 80 °C

With dmap; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; copper(l) iodide; n-butyllithium; triethylamine; In tetrahydrofuran; hexane; water; 4.1: Sonogashira reaction;

DOI:10.1021/jo060606r

Reference yield:

2-methyl-2-(prop-2-yn-1-yl)cyclopentane-1,3-dione (68197-04-6) → acetic acid 2-[3-(2-formyl-phenyl)-prop-2-ynyl]-2-methyl-3-oxo-1-trimethylsilanylethynylcyclopentyl ester (911653-40-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -70 °C

1.2: 84 percent / tetrahydrofuran; hexane / 3 h / -70 °C

2.1: 85 percent / 4-dimethylaminopyridine; Et₃N / 20 h / 20 °C

3.1: 88 percent / PdCl₂(PPh₃)2; CuI; Et₃N / 7 h / 80 °C

With dmap; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; n-butyllithium; triethylamine; In tetrahydrofuran; hexane; 3.1: Sonogashira reaction;

DOI:10.1021/jo060606r

upstream raw materials:

3-acetoxy-2-methyl-2-prop-2-ynyl-3-trimethylsilanylethynyl-cyclopentanone

ortho-bromobenzaldehyde

3-hydroxy-2-methyl-2-prop-2-ynyl-3-trimethylsilanylethynyl-cyclopentanone

2-Methylcyclopentane-1,3-dione

Downstream raw materials:

acetic acid 1-ethynyl-2-[3-(2-formyl-phenyl)-prop-2-ynyl]-2-methyl-3-oxo-cyclopentyl ester