1-(2-trimethylsilylethynylcyclohex-1-enyl)-3-trimethylsilylbuta-1,2-dienyl acetate

Base Information

• Chemical Name: 1-(2-trimethylsilylethynylcyclohex-1-enyl)-3-trimethylsilylbuta-1,2-dienyl acetate
• CAS No.: 915378-47-1
• Molecular Formula: C₂₀H₃₂O₂Si₂
• Molecular Weight: 360.644
• Mol file: 915378-47-1.mol

Synonyms:1-(2-trimethylsilylethynylcyclohex-1-enyl)-3-trimethylsilylbuta-1,2-dienyl acetate

Chemical Property of 1-(2-trimethylsilylethynylcyclohex-1-enyl)-3-trimethylsilylbuta-1,2-dienyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2-trimethylsilylethynylcyclohex-1-enyl)-3-trimethylsilylbuta-1,2-dienyl acetate

There total 5 articles about 1-(2-trimethylsilylethynylcyclohex-1-enyl)-3-trimethylsilylbuta-1,2-dienyl acetate 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: 80.0%

1-(2-trimethylsilylethynylcyclohex-1-enyl)-3-trimethylsilylpropyn-1-one (915378-46-0) + methyllithium (917-54-4) + acetic anhydride (108-24-7) → 1-(2-trimethylsilylethynylcyclohex-1-enyl)-3-trimethylsilylbuta-1,2-dienyl acetate (915378-47-1)

Guidance literature:

methyllithium; With copper(l) iodide; In diethyl ether; at 0 ℃; for 0.0833333h;

1-(2-trimethylsilylethynylcyclohex-1-enyl)-3-trimethylsilylpropyn-1-one; acetic anhydride; In diethyl ether; at -78 - 20 ℃; for 2h;

DOI:10.1021/jo061088n

Reference yield:

2-bromocyclohex-1-ene-1-carbaldehyde (38127-47-8) → 1-(2-trimethylsilylethynylcyclohex-1-enyl)-3-trimethylsilylbuta-1,2-dienyl acetate (915378-47-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 64 percent / copper(I) iodide; triethylamine / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 3 h / 0 - 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C

2.2: 87 percent / tetrahydrofuran; hexane / -78 °C

3.1: 60 percent / manganese(IV) oxide / CH₂Cl₂ / 12 h

4.1: copper(I) iodide / diethyl ether / 0.08 h / 0 °C

4.2: 80 percent / diethyl ether / 2 h / -78 - 20 °C

With manganese(IV) oxide; copper(l) iodide; n-butyllithium; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.1: Sonogashira cross-coupling;

DOI:10.1021/jo061088n

Reference yield:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 1-(2-trimethylsilylethynylcyclohex-1-enyl)-3-trimethylsilylbuta-1,2-dienyl acetate (915378-47-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: phosphorus tribromide / CH₂Cl₂ / 1 h / 0 °C

1.2: 52 percent / CH₂Cl₂ / 24 h / 25 °C

2.1: 64 percent / copper(I) iodide; triethylamine / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 3 h / 0 - 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C

3.2: 87 percent / tetrahydrofuran; hexane / -78 °C

4.1: 60 percent / manganese(IV) oxide / CH₂Cl₂ / 12 h

5.1: copper(I) iodide / diethyl ether / 0.08 h / 0 °C

5.2: 80 percent / diethyl ether / 2 h / -78 - 20 °C

With manganese(IV) oxide; copper(l) iodide; n-butyllithium; phosphorus tribromide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.1: Vilsmier-Haack reaction / 2.1: Sonogashira cross-coupling;

DOI:10.1021/jo061088n

upstream raw materials:

1-(2-trimethylsilylethynylcyclohex-1-enyl)-3-trimethylsilylpropyn-1-one

methyllithium

acetic anhydride

1-(2-trimethylsilylethynylcyclohex-1-enyl)-3-trimethylsilylpropyn-1-ol