5-(2-METHOXYPHENYL)-3-ISOXAZOLECARBOXYLIC ACID ETHYL ESTER

Base Information

• Chemical Name: 5-(2-METHOXYPHENYL)-3-ISOXAZOLECARBOXYLIC ACID ETHYL ESTER
• CAS No.: 110578-28-4
• Molecular Formula: C13H13NO4
• Molecular Weight: 247.251
• Hs Code.: 2934999090
• Mol file: 110578-28-4.mol

Synonyms:5-(2-METHOXYPHENYL)-3-ISOXAZOLECARBOXYLIC ACID ETHYL ESTER;ethyl 5-(2-methoxyphenyl)isoxazole-3-carboxylate

Chemical Property of 5-(2-METHOXYPHENYL)-3-ISOXAZOLECARBOXYLIC ACID ETHYL ESTER

Chemical Property:

• PSA: 61.56000
• LogP: 2.52690

Purity/Quality:

5-(2-METHOXYPHENYL)-3-ISOXAZOLECARBOXYLIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-(2-METHOXYPHENYL)-3-ISOXAZOLECARBOXYLIC ACID ETHYL ESTER

There total 6 articles about 5-(2-METHOXYPHENYL)-3-ISOXAZOLECARBOXYLIC 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: 75.0%

1-ethynyl-2-methoxybenzene (767-91-9) + glycine ethyl ester hydrochloride (623-33-6) → ethyl 5-(2-methoxyphenyl)isoxazole-3-carboxylate (110578-28-4)

Guidance literature:

With tert.-butylnitrite; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium hydrogencarbonate; zinc dibromide; In tert-butyl methyl ether; at 20 ℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.0c02281

Reference yield: 74.0%

2-hydroxy-4-oxo-4-(2-methoxyphenyl)but-2-enoic acid ethyl ester (1427216-72-5) → ethyl 5-(2-methoxyphenyl)isoxazole-3-carboxylate (110578-28-4)

Guidance literature:

With hydroxylamine hydrochloride; In ethanol; for 2h; Reflux;

DOI:10.1016/j.bmc.2013.06.010

Reference yield:

1-ethynyl-2-methoxybenzene (767-91-9) + ethyl 2-chloro-2-(hydroxyimino)acetate (14337-43-0) → ethyl 5-(2-methoxyphenyl)isoxazole-3-carboxylate (110578-28-4)

Guidance literature:

With triethylamine; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2005.10.002

upstream raw materials:

1-ethynyl-2-methoxybenzene

ethyl 2-chloro-2-(hydroxyimino)acetate

o-hydroxyacetophenone

2-hydroxy-4-oxo-4-(2-methoxyphenyl)but-2-enoic acid ethyl ester

Downstream raw materials:

N-(1-adamantyl)-5-(2-methoxyphenyl)isoxazole-3-carboxamide

5-(2-methoxyphenyl)isoxazole-3-carboxylic acid

2-penten-1-one-3-amino-4-hydroxy-4-methyl-1-o-methoxyphenyl

2-[5-(2-Methoxy-phenyl)-isoxazol-3-yl]-propan-2-ol

Refernces

• 1、 Zhang, Xiao-Wei,He, Xiao-Lin,Yan, Nan,Zheng, Hong-Xing,Hu, Xiang-Guo. "Oxidize Amines to Nitrile Oxides: One Type of Amine Oxidation and Its Application to Directly Construct Isoxazoles and Isoxazolines". . p. 15726 - 15735. Retrieved 2020/11/30.
• 2、 Tourteau, Aurélien,Andrzejak, Virginie,Body-Malapel, Mathilde,Lemaire, Lucas,Lemoine, Amélie,Mansouri, Roxane,Djouina, Madjid,Renault, Nicolas,El Bakali, Jamal,Desreumaux, Pierre,Muccioli, Giulio G.,Lambert, Didier M.,Chavatte, Philippe,Rigo, Beno?t,Leleu-Chavain, Natascha,Millet, Régis. "3-Carboxamido-5-aryl-isoxazoles as new CB2 agonists for the treatment of colitis". . p. 5383 - 5394. Retrieved 2013/09/02.