Methyl 3-(3,5-dimethylisoxazol-4-yl)propanoate

Base Information

• Chemical Name: Methyl 3-(3,5-dimethylisoxazol-4-yl)propanoate
• CAS No.: 154928-90-2
• Molecular Formula: C9H13NO3
• Molecular Weight: 183.2
• DSSTox Substance ID: DTXSID801271311
• Mol file: 154928-90-2.mol

Synonyms:Methyl 3-(3,5-dimethylisoxazol-4-yl)propanoate;154928-90-2;Methyl 3-(3,5-dimethyl-1,2-oxazol-4-yl)propanoate;SCHEMBL4182412;DTXSID801271311;MFCD08701341;AKOS003673052;AS-41123;Methyl 3,5-dimethyl-4-isoxazolepropanoate;CS-0328648;Methyl3-(3,5-dimethylisoxazol-4-yl)propanoate

Chemical Property of Methyl 3-(3,5-dimethylisoxazol-4-yl)propanoate

Chemical Property:

• PSA: 52.33000
• LogP: 1.39700
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 183.08954328
• Heavy Atom Count: 13
• Complexity: 184

Purity/Quality:

95% ^*data from raw suppliers

Methyl3-(3,5-Dimethylisoxazol-4-yl)propanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=NO1)C)CCC(=O)OC

Technology Process of Methyl 3-(3,5-dimethylisoxazol-4-yl)propanoate

There total 3 articles about Methyl 3-(3,5-dimethylisoxazol-4-yl)propanoate 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: 91.0%

methyl 4-acetyl-5-oxohexanoate (13984-53-7) → Methyl β-(3,5-dimethyl-4-isoxazolyl)propionate (154928-90-2)

Guidance literature:

With hydroxylamine hydrochloride; In methanol; water; for 12h; Heating;

DOI:10.1021/jo00089a037

Reference yield:

acetylacetone (123-54-6,81235-32-7) → Methyl β-(3,5-dimethyl-4-isoxazolyl)propionate (154928-90-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / t-BuOK / 2-methyl-propan-2-ol / 20 h / Ambient temperature

2: 91 percent / hydroxylamine hydrochloride / H₂O; methanol / 12 h / Heating

With hydroxylamine hydrochloride; potassium tert-butylate; In methanol; water; tert-butyl alcohol;

DOI:10.1021/jo00089a037

Reference yield:

acetylacetone (123-54-6,81235-32-7) → Methyl β-(3,5-dimethyl-4-isoxazolyl)propionate (154928-90-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 0.33 h / 55 °C

1.2: 18 h / 55 °C

2.1: hydroxylamine hydrochloride / water; methanol / 18 h / Reflux

With hydroxylamine hydrochloride; potassium carbonate; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jm500066b

upstream raw materials:

methyl 4-acetyl-5-oxohexanoate

acetylacetone

Downstream raw materials:

2-(3,5-dimethylisoxazol-4-yl)acetic acid

3-(3,5-dimethyl-4-isoxazolyl)propanoyl chloride

β-(3,5-Dimethyl-4-isoxazolyl)propionic acid

Refernces

• 1、 Ceccherelli, Paolo,Curini, Massimo,Marcotullio, Maria Carla,Rosati, Ornelio,Wenkert, Ernest. "Metal-Catalyzed, Intramolecular Reactions of α-Diazo Ketones with Isoxazoles". . p. 2882 - 2884. Retrieved 2007/10/02.