ETHYL (2E)-4-HYDROXY-BUT-2-ENOATE

Base Information

• Chemical Name: ETHYL (2E)-4-HYDROXY-BUT-2-ENOATE
• CAS No.: 10080-68-9
• Molecular Formula: C6H10O3
• Molecular Weight: 130.144
• Hs Code.: 2918199090
• Mol file: 10080-68-9.mol

Synonyms:(E)-4-Hydroxycrotonoic Acid Ethyl Ester;

Chemical Property of ETHYL (2E)-4-HYDROXY-BUT-2-ENOATE

Chemical Property:

• Boiling Point: 119-120 °C(Press: 13 Torr)
• PKA: 13.29±0.10(Predicted)
• PSA: 46.53000
• Density: 1.077 g/cm3
• LogP: 0.09800
• Storage Temp.: Refrigerator
• Solubility.: DCM, Ethyl Acetate

Purity/Quality:

98%,99%, ^*data from raw suppliers

(E)-4-HydroxycrotonoicAcidEthylEster(~85%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (E)-4-Hydroxycrotonoic Acid Ethyl Ester is an intermediate in the preparation of unusual amino acids that are potential Michael acceptor based antiplasmodial and antitrypanosomal cysteine protease inhibitors.

Technology Process of ETHYL (2E)-4-HYDROXY-BUT-2-ENOATE

There total 25 articles about ETHYL (2E)-4-HYDROXY-BUT-2-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: 100.0%

(+/-)-ethyl-3,4-epoxybutanoate (32223-97-5) → (E)-ethyl 4-hydroxybut-2-enoate (10080-68-9)

Guidance literature:

With base; In tetrahydrofuran; Ambient temperature;

DOI:10.1039/c39860000836

Reference yield: 88.0%

fumaric acid ethyl ester mono chloride (26367-48-6) → (E)-ethyl 4-hydroxybut-2-enoate (10080-68-9)

Guidance literature:

With zinc(II) tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1246/bcsj.61.2684

Reference yield: 85.0%

ethyl 4-chloro-3-hydroxybutanoate (86728-85-0,87068-18-6,90866-33-4,10488-69-4) → (E)-ethyl 4-hydroxybut-2-enoate (10080-68-9)

Guidance literature:

With sodium hydroxide; In ethanol; at 0 - 20 ℃; for 15h;

upstream raw materials:

ethyl 4-chloro-3-hydroxybutanoate

ethanol

(2E)-4-hydroxybut-2-enoic acid

4-bromo-trans-crotonic acid ethyl ester

Downstream raw materials:

ethyl (E)-4-chlorobut-2-enoate

4-(4-nitro-benzoyloxy)-trans-crotonic acid ethyl ester

4-oxo-but-2-enoic acid ethyl ester

(4R,5R)-5-Hydroxymethyl-3-phenyl-4,5-dihydro-isoxazole-4-carboxylic acid ethyl ester

Refernces

• 1、 Liang, Yu-Fu,Chung, Chuang-Chung,Huang, Meng-Wen,Uang, Biing-Jiun. "Formal syntheses of (?)-isoretronecanol, (+)-laburnine, and a concise enantioselective synthesis of (+)-turneforcidine". . p. 397 - 406. Retrieved 2019.
• 2、 De Angelis, Martina,Sappino, Carla,Mandic, Emanuela,D'Alessio, Marianna,De Dominicis, Maria Grazia,Sannino, Sara,Primitivo, Ludovica,Mencarelli, Paolo,Ricelli, Alessandra,Righi, Giuliana. "Stereodivergent synthesis of piperidine iminosugars 1-deoxy-D-nojirimycin and 1-deoxy-D-altronojirimycin". . . Retrieved 2020/12/21.
• 3、 Heckenbichler, Kathrin,Schweiger, Anna,Brandner, Lea Alexandra,Binter, Alexandra,Toplak, Marina,Macheroux, Peter,Gruber, Karl,Breinbauer, Rolf. "Asymmetric Reductive Carbocyclization Using Engineered Ene Reductases". supporting information. p. 7240 - 7244. Retrieved 2018/06/15.