4-Pentenoic acid, 3-hydroxy-, ethyl ester

Base Information

• Chemical Name: 4-Pentenoic acid, 3-hydroxy-, ethyl ester
• CAS No.: 38996-01-9
• Molecular Formula: C7H12 O3
• Molecular Weight: 144.17
• Hs Code.: 2918199090
• Mol file: 38996-01-9.mol

Synonyms:3-Hydroxypent-4-enoicacid ethyl ester; Ethyl 3-hydroxy-4-pentenoate

Chemical Property of 4-Pentenoic acid, 3-hydroxy-, ethyl ester

Chemical Property:

• Refractive Index: 1.4393 (589.3 nm 30℃)
• Boiling Point: 63-64℃ (2 Torr)
• PSA: 46.53000
• LogP: 0.48650

Purity/Quality:

98%min ^*data from raw suppliers

4-Pentenoicacid,3-hydroxy-,ethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Pentenoic acid, 3-hydroxy-, ethyl ester

There total 4 articles about 4-Pentenoic acid, 3-hydroxy-, 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: 99.0%

lithium 1-ethoxyethenolate (56579-97-6) + acrolein (107-02-8,25068-14-8) → ethyl 3-hydroxypent-4-enoate (38996-01-9)

Guidance literature:

at -78 ℃;

DOI:10.1016/S0040-4039(96)02020-5

Reference yield: 95.0%

ethyl acetate (141-78-6) + acrolein (107-02-8,25068-14-8) → ethyl 3-hydroxypent-4-enoate (38996-01-9)

Guidance literature:

ethyl acetate; With n-butyllithium; isopropylamine; In tetrahydrofuran; at -78 ℃; for 0.75h; Inert atmosphere;

acrolein; In tetrahydrofuran; at -78 ℃; for 0.25h; Inert atmosphere;

DOI:10.1016/j.tet.2019.130593

Reference yield: 60.0%

ethyl bromoacetate (105-36-2) + acrolein (107-02-8,25068-14-8) → ethyl 3-hydroxypent-4-enoate (38996-01-9)

Guidance literature:

With zinc; In benzene;

DOI:10.1016/S0040-4039(99)00376-7

upstream raw materials:

ethyl bromoacetate

acrolein

ethyl acetate

lithium 1-ethoxyethenolate

Downstream raw materials:

3-(tert-butyldiphenylsilyloxy)pent-4-eneoic acid ethyl ester

(E)-ethyl 3-hydroxy-5-phenylpent-4-enoate

ethyl 3-oxo-5-phenylpentanoate

4a-methyl-2,5-dioxo-2,3,4,4a,5,6,7,8-octahydro-[1]naphthoic acid ethyl ester

Refernces

• 1、 Kempter, Irina,Schur, Christine,Huttenlochner, Katharina,Bergstr??er, Ruth-Maria,Wolff, Benjamin,Kopf, Thomas,Hartung, Jens. "2,3-cis-Cyclization of 4-pentenoxyl radicals". . p. 7699 - 7714. Retrieved 2016.
• 2、 Davison, Emma K.,Hume, Paul A.,Sperry, Jonathan. "Total Synthesis of an Isatis indigotica-Derived Alkaloid Using a Biomimetic Thio-Diels-Alder Reaction". . p. 3545 - 3548. Retrieved 2018.
• 3、 Kim, Taehyeong,Lee, Sung Il,Kim, Sejin,Shim, Su Yong,Ryu, Do Hyun. "Total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α via three-component coupling". supporting information. . Retrieved 2019/09/17.
• 4、 Escudero, Julien,Bellosta, Véronique,Cossy, Janine. "Rhodium-Catalyzed Cyclization of O,ω-Unsaturated Alkoxyamines: Formation of Oxygen-Containing Heterocycles". supporting information. p. 574 - 578. Retrieved 2018/02/21.