Ethyl 2-methyl-3-oxohexanoate

Base Information

• Chemical Name: Ethyl 2-methyl-3-oxohexanoate
• CAS No.: 29304-40-3
• Molecular Formula: C9H16 O3
• Molecular Weight: 172.224
• Hs Code.: 2918300090
• European Community (EC) Number: 842-567-4
• DSSTox Substance ID: DTXSID90951875
• Nikkaji Number: J102.413B
• Mol file: 29304-40-3.mol

Synonyms:ETHYL 2-METHYL-3-OXOHEXANOATE;29304-40-3;Hexanoic acid, 2-methyl-3-oxo-, ethyl ester;2-METHYL-3-OXO-HEXANOIC ACID ETHYL ESTER;2-METHYL-3-OXO-HEXANOICACIDETHYLESTER;SCHEMBL4939835;DTXSID90951875;Ethyl 2-methyl-3-oxohexanoate #;ZHDUQUQKEAZVPG-UHFFFAOYSA-N;AKOS006274886;2-Methyl-3-oxohexanoic acid ethyl ester;CS-0232774;FT-0693312;EN300-128625;Z1198149929

Chemical Property of Ethyl 2-methyl-3-oxohexanoate

Chemical Property:

• Vapor Pressure: 0.167mmHg at 25°C
• Boiling Point: 213.2°Cat760mmHg
• Flash Point: 82.4°C
• PSA: 43.37000
• Density: 0.967g/cm³
• LogP: 1.55480
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 172.109944368
• Heavy Atom Count: 12
• Complexity: 163

Purity/Quality:

99%min ^*data from raw suppliers

ethyl2-methyl-3-oxohexanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(=O)C(C)C(=O)OCC

Technology Process of Ethyl 2-methyl-3-oxohexanoate

There total 19 articles about Ethyl 2-methyl-3-oxohexanoate 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: 72.0%

2-acetylpropanoic acid ethyl ester (609-14-3) + ethyl iodide (75-03-6) → 2-methyl-3-oxohexanoic acid ethyl ester (29304-40-3)

Guidance literature:

With n-butyllithium; sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1016/0040-4039(96)00483-2

Reference yield: 61.0%

2-acetylpropanoic acid ethyl ester (609-14-3) → 2-methyl-3-oxohexanoic acid ethyl ester (29304-40-3)

Guidance literature:

2-acetylpropanoic acid ethyl ester; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃;

With n-butyllithium; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.666667h;

ethyl halide; Further stages;

DOI:10.1016/j.tet.2010.06.084

Reference yield: 60.0%

1-(pyrrolidin-1-yl)butane-1-thione (66343-95-1) + Ethyl 2-bromopropionate (535-11-5,41978-69-2) → 2-methyl-3-oxohexanoic acid ethyl ester (29304-40-3) + 2-[1-(ethoxycarbonyl)ethylsulfanyl]propanoic acid ethyl ester (14936-00-6)

Guidance literature:

1-(pyrrolidin-1-yl)butane-1-thione; Ethyl 2-bromopropionate; at 80 ℃;

With triethylamine; Hexamethylphosphorous triamide; In acetonitrile; Heating;

DOI:10.1139/v04-088

upstream raw materials:

methyl bromide

ethyl butyroyl acetate

methyl iodide

2-acetylpropanoic acid ethyl ester

Downstream raw materials:

(E)-4-Methyl-5-phenyl-pent-4-enoic acid [2-(tert-butyl-dimethyl-silanyloxy)-1-(3-ethyl-6-methoxy-5-methyl-4-oxo-4H-pyran-2-yl)-ethyl]-amide

(E)-4-Methyl-5-phenyl-pent-4-enoic acid 2-(3-ethyl-6-methoxy-5-methyl-4-oxo-4H-pyran-2-yl)-2-oxo-ethyl ester

(E)-4-Methyl-5-phenyl-pent-4-enoic acid 2-(3-ethyl-6-methoxy-5-methyl-4-oxo-4H-pyran-2-yl)-2-hydroxy-ethyl ester

(E)-4-Methyl-5-phenyl-pent-4-enoic acid [1-(3-ethyl-6-methoxy-5-methyl-4-oxo-4H-pyran-2-yl)-2-hydroxy-ethyl]-amide

Refernces

• 1、 Chan, Yinman,Balle, Jared,Kevin Sparrow,Boyd, Peter D.W.,Brimble, Margaret A.,Barker, David. "A double Mannich approach to the synthesis of substituted piperidones - Application to the synthesis of substituted E-ring analogues of methyllycaconitine". experimental part. p. 7179 - 7191. Retrieved 2010/10/01.
• 2、 Bellec, Christian,Gaurat, Olivier. "A new efficient synthesis of α-methyl-β-ketoesters through an Eschenmoser sulfide reaction". . p. 1289 - 1293. Retrieved 2007/10/03.