5-phenyl-penta-2,3-dienoic acid ethyl ester

Base Information

• Chemical Name: 5-phenyl-penta-2,3-dienoic acid ethyl ester
• CAS No.: 935254-77-6
• Molecular Formula: C₁₃H₁₄O₂
• Molecular Weight: 202.253
• Mol file: 935254-77-6.mol

Synonyms:5-phenyl-penta-2,3-dienoic acid ethyl ester

Chemical Property of 5-phenyl-penta-2,3-dienoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-phenyl-penta-2,3-dienoic acid ethyl ester

There total 3 articles about 5-phenyl-penta-2,3-dienoic 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: 93.0%

hydrocinnamic acid chloride (645-45-4) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → 5-phenyl-penta-2,3-dienoic acid ethyl ester (935254-77-6)

Guidance literature:

ethyl (triphenylphosphoranylidene)acetate; With triethylamine; In dichloromethane; for 10h; Inert atmosphere;

hydrocinnamic acid chloride; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol901334c

Reference yield:

diazoacetic acid ethyl ester (623-73-4) + propargyl benzene (10147-11-2) → 5-phenyl-penta-2,3-dienoic acid ethyl ester (935254-77-6)

Guidance literature:

With copper(l) iodide; In acetonitrile; at 20 ℃; for 12h;

DOI:10.1002/anie.200454070

Reference yield:

ethyl (E)-5-phenyl-3-(trifluoromethylsulfonyloxy)pent-2-enoate (122135-98-2) → 5-phenyl-penta-2,3-dienoic acid ethyl ester (935254-77-6) + ethyl 5-phenylpent-3-ynoate

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triisopropyl phosphite; N-ethyl-N,N-diisopropylamine; In Isopropyl acetate; at 50 ℃; Overall yield = 69 %; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.7b02736

upstream raw materials:

diazoacetic acid ethyl ester

propargyl benzene

hydrocinnamic acid chloride

ethyl (triphenylphosphoranylidene)acetate

Downstream raw materials:

ethyl (2E,4E)-5-phenyl-penta-2,4-dienoate

ethyl (3E,4E)-5-phenyl-3-(pyridin-2-ylmethylene)pent-4-enoate

ethyl (3E,4E)-5-phenyl-3-(pyridin-4-ylmethylene)pent-4-enoate

(3E,4E)-ethyl 5-phenyl-3-[(pyridin-3-yl)methylene]pent-4-enoate

Refernces

• 1、 El Arba, Marie,Dibrell, Sara E.,Crouch, Ian T.,Frantz, Doug E.. "Unified approach to substituted allenoates via Pd-catalyzed β-hydride elimination of (E)-enol triflates". supporting information. p. 5446 - 5449. Retrieved 2017/11/06.
• 2、 Li, Erqing,Huang, You. "Phosphine-catalyzed domino reaction: A novel sequential [2+3] and [3+2] annulation reaction of γ-substituent allenoates to construct bicyclic[3, 3, 0]octene derivatives". supporting information. p. 948 - 950. Retrieved 2014/01/06.