Ethyl 3-methyl-4-oxopent-2-enoate

Base Information

• Chemical Name: Ethyl 3-methyl-4-oxopent-2-enoate
• CAS No.: 13979-23-2
• Molecular Formula: C8H12O3
• Molecular Weight: 156.1791
• NSC Number: 157344
• Nikkaji Number: J435.910K,J695.562B
• Mol file: 13979-23-2.mol

Synonyms:ethyl 3-methyl-4-oxopent-2-enoate;13979-23-2;ethyl (E)-3-methyl-4-oxopent-2-enoate;107368-27-4;2-Pentenoic acid, 3-methyl-4-oxo-, ethyl ester, (Z)-;NSC157344;ethyl3-methyl-4-oxopent-2-enoate;NSC-157344;3-Methyl-4-oxo-2-pentenoic acid ethyl ester;EN300-205860;(E)-3-Methyl-4-oxo-2-pentenoic acid ethyl ester

Chemical Property of Ethyl 3-methyl-4-oxopent-2-enoate

Chemical Property:

• Vapor Pressure: 0.045mmHg at 25°C
• Boiling Point: 237.4°C at 760 mmHg
• Flash Point: 98°C
• Density: 1.01g/cm³
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 156.078644241
• Heavy Atom Count: 11
• Complexity: 192

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=C(C)C(=O)C
• Isomeric SMILES: CCOC(=O)/C=C(\C)/C(=O)C

Technology Process of Ethyl 3-methyl-4-oxopent-2-enoate

There total 5 articles about Ethyl 3-methyl-4-oxopent-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: 34.0%

ketene diethyl acetal (2678-54-8) + dimethylglyoxal (431-03-8) → 3-methyl-4-oxo-2-pentenoic acid ethyl ester (13979-23-2) + 3-hydroxy-3-methyl-levulinic acid ethylester (67079-92-9) + 2,2-diethoxy-4-acetyl-4-methyl-oxetane (93183-68-7) + 3-ethoxy-5-acetyl-5-methyl-2-(E),4(E)-pentadienoic acid ethyl ester (96746-42-8)

Guidance literature:

In acetonitrile; for 72h; Yield given. Further byproducts given; Ambient temperature;

DOI:10.1021/jo00216a002

Reference yield: 34.0%

ketene diethyl acetal (2678-54-8) + dimethylglyoxal (431-03-8) → 3-methyl-4-oxo-2-pentenoic acid ethyl ester (13979-23-2) + 3-hydroxy-3-methyl-levulinic acid ethylester (67079-92-9) + 2,2-diethoxy-4-acetyl-4-methyl-oxetane (93183-68-7) + 3-ethoxy-5-acetyl-5-methyl-2-(E),4(Z)-pentadienoic acid ethyl ester (96746-41-7) + 3-ethoxy-5-acetyl-5-methyl-2-(E),4(E)-pentadienoic acid ethyl ester (96746-42-8)

Guidance literature:

In acetonitrile; for 72h; Product distribution; Mechanism; Ambient temperature; other 1,2-diketones;

DOI:10.1021/jo00216a002

Reference yield:

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + dimethylglyoxal (431-03-8) → 3-methyl-4-oxo-2-pentenoic acid ethyl ester (13979-23-2)

Guidance literature:

With sodium hydride; In diethyl ether;

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

dimethylglyoxal

1-ethoxyacetylene

ketene diethyl acetal