(E)-ethyl 5-phenylhex-4-enoate

Base Information

• Chemical Name: (E)-ethyl 5-phenylhex-4-enoate
• CAS No.: 1338046-10-8
• Molecular Formula: C₁₄H₁₈O₂
• Molecular Weight: 218.296
• Mol file: 1338046-10-8.mol

Synonyms:(E)-ethyl 5-phenylhex-4-enoate

Chemical Property of (E)-ethyl 5-phenylhex-4-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-ethyl 5-phenylhex-4-enoate

There total 5 articles about (E)-ethyl 5-phenylhex-4-enoate 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: 98.0%

ethanol (64-17-5) + (E)-5-phenylhex-4-enoic acid (132179-72-7,28525-63-5,91764-08-8) → (E)-ethyl 5-phenylhex-4-enoate (1338046-10-8)

Guidance literature:

With toluene-4-sulfonic acid; In chloroform; for 26h; Reflux;

DOI:10.1016/j.tet.2012.05.013

Reference yield: 90.0%

(E)-ethyl 5-phenyl-2-hexenoate (83565-88-2) → (E)-ethyl 5-phenylhex-4-enoate (1338046-10-8)

Guidance literature:

With C₁₉H₄₄ClP₂Pd; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; In toluene; at 80 ℃; for 16h; diastereoselective reaction; Sealed tube; Inert atmosphere; Glovebox; Schlenk technique;

DOI:10.1021/jacs.9b09373

Reference yield:

(E)-(5-bromopent-2-en-2-yl)benzene (3574-91-2,128902-50-1) → (E)-ethyl 5-phenylhex-4-enoate (1338046-10-8)

Guidance literature:

Multi-step reaction with 3 steps

1: dimethyl sulfoxide / 18 h / 100 °C

2: water; potassium hydroxide / ethylene glycol / 10 h / 100 °C

3: toluene-4-sulfonic acid / chloroform / 26 h / Reflux

With water; toluene-4-sulfonic acid; potassium hydroxide; In chloroform; ethylene glycol; dimethyl sulfoxide;

DOI:10.1016/j.tet.2012.05.013

upstream raw materials:

Cyclopropyl methyl ketone

ethanol

(E)-5-phenylhex-4-enoic acid

(E)-(5-bromopent-2-en-2-yl)benzene

Downstream raw materials:

ethyl (E)-2-(2'-hydroxyprop-2'-yl)-5-phenyl-4-hexenoate

Refernces

• 1、 Brücher, Oliver,Bergstr??er, Uwe,Kelm, Harald,Hartung, Jens,Greb, Marco,Svoboda, Ingrid,Fuess, Hartmut. "Controlling 6-endo-selectivity in oxidation/bromocyclization cascades for synthesis of aplysiapyranoids and other 2,2,6,6-substituted tetrahydropyrans". . p. 6968 - 6980. Retrieved 2012/09/07.