Propanoic acid, 2,2-dimethyl-, [2-[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-3-oxo-1-cyclohexen-1- yl]methyl ester

Base Information

• Chemical Name: Propanoic acid, 2,2-dimethyl-, [2-[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-3-oxo-1-cyclohexen-1- yl]methyl ester
• CAS No.: 193334-92-8
• Molecular Formula: C24H36O4Si
• Molecular Weight: 416.633
• Mol file: 193334-92-8.mol

Synonyms:

Chemical Property of Propanoic acid, 2,2-dimethyl-, [2-[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-3-oxo-1-cyclohexen-1- yl]methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Propanoic acid, 2,2-dimethyl-, [2-[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-3-oxo-1-cyclohexen-1- yl]methyl ester

There total 2 articles about Propanoic acid, 2,2-dimethyl-, [2-[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-3-oxo-1-cyclohexen-1- yl]methyl 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: 81.0%

(2-iodo-3-oxocyclohex-1-en-1-yl)methyl pivalate (181041-43-0) + (3-(tri-n-butylstannyl)phenoxy)(tert-butyl)dimethylsilane → 2,2-Dimethyl-propionic acid 2-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-oxo-cyclohex-1-enylmethyl ester (193334-92-8)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; copper(l) iodide; triphenyl-arsane; In various solvent(s); at 70 ℃; for 22h;

DOI:10.1016/S0040-4020(97)00616-9

Reference yield:

(3-oxocyclohex-1-en-1-yl)methyl pivalate (123290-35-7) → 2,2-Dimethyl-propionic acid 2-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-oxo-cyclohex-1-enylmethyl ester (193334-92-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Me₃SiN₃, 2.) I₂, pyridine / 1.) CCl₄, 0 deg C, 3 h, 2.) CCl₄, room temperature, 22 h

2: 81 percent / CuI, AsPh₃, Pd₂(dba)3*CHCl₃ / various solvent(s) / 22 h / 70 °C

With pyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; copper(l) iodide; triphenyl-arsane; trimethylsilylazide; iodine; In various solvent(s);

DOI:10.1016/S0040-4020(97)00616-9

Reference yield:

2,2-Dimethyl-propionic acid 2-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-oxo-cyclohex-1-enylmethyl ester (193334-92-8) → 14-(3-hydroxyphenyl)-9-methoxy-13-oxatricyclo[7.3.2.01,14]-tetradec-5-ene-3,7-diyne-2-ol

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) n-BuLi / 1.) THF, hexane, -50 deg C, 1 h, 2.) THF, hexane, -78 deg C, 2 h

2: 1.) NaH, 2.) 1,3-dimethyl-2-imidazolidinone / 1.) THF, 0 deg C, 5 min, 2.) THF, room temperature, 1 h

3: 1.) AgNO₃, 2.) KCN / 1.) THF, EtOH, H₂O, 0 deg C, 25 min, 2.) THF, EtOH, H₂O, room temperature, 1 h

4: 77 percent / CuI, Pd₂(dba)3*CHCl₃, n-butylamine / benzene / 1.) 0 deg C, 1 h, 2.) room temperature, 20 h

5: 85 percent / DIBAH / toluene / 1 h / -78 °C

6: 97 percent / mCPBA, Na₂HPO₄ / CH₂Cl₂ / 18 h / 0 - 20 °C

7: 1.) AgNO₃, 2.) KCN / 1.) THF, ethanol, water, 0 deg C, 20 min, 2.) THF, ethanol, water, 0 deg C - 0.5 h, room temperature - 0.5 h

8: 83 percent / Dess-Martin periodinate / CH₂Cl₂ / 1.5 h / Ambient temperature

9: 28 percent / bis-(trimethylsilyl)potassium amide / tetrahydrofuran; toluene / 2 h / -78 °C

10: 81 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h / 0 °C

With 1,3-dimethyl-2-imidazolidinone; potassium cyanide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; disodium hydrogenphosphate; copper(l) iodide; n-butyllithium; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; silver nitrate; N-butylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; toluene; benzene;

DOI:10.1016/S0040-4020(97)00616-9

upstream raw materials:

(2-iodo-3-oxocyclohex-1-en-1-yl)methyl pivalate

(3-oxocyclohex-1-en-1-yl)methyl pivalate