4,5-Isoxazoledicarboxylic acid, 2,3-dihydro-2-methyl-3-phenyl-, dimethyl ester

Base Information

• Chemical Name: 4,5-Isoxazoledicarboxylic acid, 2,3-dihydro-2-methyl-3-phenyl-, dimethyl ester
• CAS No.: 109787-18-0
• Molecular Formula: C14H15NO5
• Molecular Weight: 277.277
• Mol file: 109787-18-0.mol

Synonyms:

Chemical Property of 4,5-Isoxazoledicarboxylic acid, 2,3-dihydro-2-methyl-3-phenyl-, dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4,5-Isoxazoledicarboxylic acid, 2,3-dihydro-2-methyl-3-phenyl-, dimethyl ester

There total 9 articles about 4,5-Isoxazoledicarboxylic acid, 2,3-dihydro-2-methyl-3-phenyl-, dimethyl 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: 94.0%

C-phenyl-N-methylnitrone (3376-23-6,7372-59-0,59862-60-1) + dimethyl acetylenedicarboxylate (762-42-5) → 2-methyl-3-phenyl-4,5-dicarbomethoxy-Δ4-isoxazoline (109787-18-0)

Guidance literature:

With 1-butyl-3-methylimidazolium Tetrafluoroborate; at 20 ℃; for 0.25h;

DOI:10.1002/jhet.682

Reference yield: 92.0%

N-methyl-α-phenylnitrone (3376-23-6) + dimethyl acetylenedicarboxylate (762-42-5) → 2-methyl-3-phenyl-4,5-dicarbomethoxy-Δ4-isoxazoline (109787-18-0)

Guidance literature:

With titanium tetrachloride; at 20 ℃; for 0.05h; neat (no solvent);

DOI:10.1080/00397910903537349

Reference yield:

dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate (947-57-9) + N-methyl-α-phenylnitrone (3376-23-6) → cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + 2-methyl-3-phenyl-4,5-dicarbomethoxy-Δ4-isoxazoline (109787-18-0)

Guidance literature:

In benzene; for 240h; Yield given; Heating;

DOI:10.1016/S0040-4020(01)92451-2

upstream raw materials:

dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate

N-methyl-α-phenylnitrone

7-isopropylidene-2,3-dicarbomethoxynorbornadiene

dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate

Downstream raw materials:

methyl 4-phenyl-3-carbomethoxy-2-oxo-3-butenoate

Refernces

• 1、 Valizadeh, Hassan,Dinparast, Leila. "Rapid, highly efficient, and room-temperature TiCl4-catalyzed synthesis of 4-Isoxazolines under Solvent-Free Conditions". experimental part. p. 291 - 297. Retrieved 2011/03/20.
• 2、 Padwa, Albert,Dent, William H.,Schoffstall, Allen M.,Yeske, Philip E.. "Silyl Group Transfer in the Cycloaddiition Reactions of Silyl Iminium Salts Derived from Aryl-Substituted Oximes". . p. 4430 - 4437. Retrieved 2007/10/02.