(2Z,6E)-3-(4-Fluoro-phenyl)-7,11-dimethyl-dodeca-2,6,10-trienoic acid ethyl ester

Base Information

• Chemical Name: (2Z,6E)-3-(4-Fluoro-phenyl)-7,11-dimethyl-dodeca-2,6,10-trienoic acid ethyl ester
• CAS No.: 298681-43-3
• Molecular Formula: C₂₂H₂₉FO₂
• Molecular Weight: 344.469
• Mol file: 298681-43-3.mol

Synonyms:(2Z,6E)-3-(4-Fluoro-phenyl)-7,11-dimethyl-dodeca-2,6,10-trienoic acid ethyl ester

Chemical Property of (2Z,6E)-3-(4-Fluoro-phenyl)-7,11-dimethyl-dodeca-2,6,10-trienoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2Z,6E)-3-(4-Fluoro-phenyl)-7,11-dimethyl-dodeca-2,6,10-trienoic acid ethyl ester

There total 2 articles about (2Z,6E)-3-(4-Fluoro-phenyl)-7,11-dimethyl-dodeca-2,6,10-trienoic acid ethyl 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: 44.0%

ethyl (2Z,6E)-7,11-dimethyl-3-(trifluoromethylsulfonyloxy)-2,6,10-dodecatrienoate (157327-74-7) → (2Z,6E)-3-(4-Fluoro-phenyl)-7,11-dimethyl-dodeca-2,6,10-trienoic acid ethyl ester (298681-43-3)

Guidance literature:

4-fluorophenyl-MgX X=Cl, Br, I; With CuCN; In diethyl ether; at 0 ℃; for 0.0833333h;

ethyl (2Z,6E)-7,11-dimethyl-3-(trifluoromethylsulfonyloxy)-2,6,10-dodecatrienoate; In tetrahydrofuran; diethyl ether; at -78 ℃; for 2.5h;

DOI:10.1016/S0960-894X(00)00337-1

Reference yield:

ethyl (6E)-7,11-dimethyl-3-oxo-6,10-dodecadienoate (59633-02-2) → (2Z,6E)-3-(4-Fluoro-phenyl)-7,11-dimethyl-dodeca-2,6,10-trienoic acid ethyl ester (298681-43-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (Me₃Si)2NK / tetrahydrofuran

1.2: 64 percent / tetrahydrofuran

2.1: CuCN / diethyl ether / 0.08 h / 0 °C

2.2: 44 percent / diethyl ether; tetrahydrofuran / 2.5 h / -78 °C

With potassium hexamethylsilazane; In tetrahydrofuran; diethyl ether; 1.1: Metallation / 1.2: triflation / 2.1: complexation / 2.2: coupling;

DOI:10.1016/S0960-894X(00)00337-1

Reference yield:

(2Z,6E)-3-(4-Fluoro-phenyl)-7,11-dimethyl-dodeca-2,6,10-trienoic acid ethyl ester (298681-43-3) → (2Z,6E)-3-(4-Fluoro-phenyl)-7,11-dimethyl-dodeca-2,6,10-trien-1-ol (298681-51-3)

Guidance literature:

With diisobutylaluminium hydride; In toluene;

DOI:10.1016/S0960-894X(00)00337-1

upstream raw materials:

ethyl (2Z,6E)-7,11-dimethyl-3-(trifluoromethylsulfonyloxy)-2,6,10-dodecatrienoate

ethyl (6E)-7,11-dimethyl-3-oxo-6,10-dodecadienoate

Downstream raw materials:

(2Z,6E)-3-(4-Fluoro-phenyl)-7,11-dimethyl-dodeca-2,6,10-trien-1-ol