ethyl (S,E)-5-methyl-5-phenylhepta-2,6-dienoate

Base Information

• Chemical Name: ethyl (S,E)-5-methyl-5-phenylhepta-2,6-dienoate
• CAS No.: 1311260-45-3
• Molecular Formula: C₁₆H₂₀O₂
• Molecular Weight: 244.334
• Mol file: 1311260-45-3.mol

Synonyms:ethyl (S,E)-5-methyl-5-phenylhepta-2,6-dienoate

Chemical Property of ethyl (S,E)-5-methyl-5-phenylhepta-2,6-dienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (S,E)-5-methyl-5-phenylhepta-2,6-dienoate

There total 10 articles about ethyl (S,E)-5-methyl-5-phenylhepta-2,6-dienoate 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: 86.0%

(S)-(3-methylhexa-1,5-dien-3-yl)benzene (1301717-32-7) + ethyl acrylate (140-88-5,9003-32-1) → ethyl (S,E)-5-methyl-5-phenylhepta-2,6-dienoate (1311260-45-3)

Guidance literature:

With Hoveyda-Grubbs catalyst second generation; In dichloromethane; at 40 ℃; for 14h; Inert atmosphere;

DOI:10.1021/ja2039248

Reference yield:

acetophenone (98-86-2) → ethyl (S,E)-5-methyl-5-phenylhepta-2,6-dienoate (1311260-45-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-butyllithium / hexane / 0.5 h / 0 °C

1.2: Inert atmosphere; Reflux

2.1: diisobutylaluminium hydride / dichloromethane / 0 °C / Inert atmosphere

3.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / dichloromethane; water / 20 °C / Inert atmosphere

4.1: tris-(dibenzylideneacetone)dipalladium(0); (R)-(+)-2,2′-bis(di-2-furanylphosphino)-6,6′-dimethoxy-1,1′-biphenyl; cesium fluoride / tetrahydrofuran; water / 36 h / 60 °C / Inert atmosphere

5.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 14 h / 40 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; Hoveyda-Grubbs catalyst second generation; (R)-(+)-2,2′-bis(di-2-furanylphosphino)-6,6′-dimethoxy-1,1′-biphenyl; tetra(n-butyl)ammonium hydrogensulfate; diisobutylaluminium hydride; cesium fluoride; sodium hydroxide; In tetrahydrofuran; hexane; dichloromethane; water;

DOI:10.1021/ja2039248

Reference yield:

tert-butyl (2-phenylbut-3-en-2-yl) carbonate (1311260-02-2) → ethyl (S,E)-5-methyl-5-phenylhepta-2,6-dienoate (1311260-45-3)

Guidance literature:

Multi-step reaction with 2 steps

1: tris-(dibenzylideneacetone)dipalladium(0); (R)-(+)-2,2′-bis(di-2-furanylphosphino)-6,6′-dimethoxy-1,1′-biphenyl; cesium fluoride / tetrahydrofuran; water / 12 h / 60 °C / Inert atmosphere

2: Hoveyda-Grubbs catalyst second generation / dichloromethane / 14 h / 40 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; Hoveyda-Grubbs catalyst second generation; (R)-(+)-2,2′-bis(di-2-furanylphosphino)-6,6′-dimethoxy-1,1′-biphenyl; cesium fluoride; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ja2039248

upstream raw materials:

(S)-(3-methylhexa-1,5-dien-3-yl)benzene

ethyl acrylate

tert-butyl ((E)-3-phenylbut-2-en-1-yl) carbonate

tert-butyl (2-phenylbut-3-en-2-yl) carbonate