Ethyl 3-methyl-4-oxopentanoate

Base Information

• Chemical Name: Ethyl 3-methyl-4-oxopentanoate
• CAS No.: 55424-74-3
• Molecular Formula: C8H14O3
• Molecular Weight: 158.197
• DSSTox Substance ID: DTXSID00564859
• Nikkaji Number: J919.684F
• Mol file: 55424-74-3.mol

Synonyms:ethyl 3-methyl-4-oxopentanoate;55424-74-3;SCHEMBL25975236;DTXSID00564859;BS-34535;3-methyl-4-oxo-pentanoic acid ethyl ester

Chemical Property of Ethyl 3-methyl-4-oxopentanoate

Chemical Property:

• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 158.094294304
• Heavy Atom Count: 11
• Complexity: 151

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)CC(C)C(=O)C

Technology Process of Ethyl 3-methyl-4-oxopentanoate

There total 1 articles about Ethyl 3-methyl-4-oxopentanoate 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: 39.0%

ethyl 2-(bromomethyl)-2-methyl-3-oxobutanoate (107987-07-5) → ethyl 2,2-dimethyl-3-oxobutanoate (597-04-6) + 2-methyl-4-oxo-valeric acid ethyl ester (4749-12-6) + ethyl 3-methyl-4-oxopentanoate (55424-74-3)

Guidance literature:

With cobalt complex of 2,10-diethyl-3,9-dipropyl-1,4,8,11-tetraazaundeca-1,3,8,10-tetraene-1,11-diol; electrolytic process;

DOI:10.1246/cl.1988.835

Reference yield: 50.0%

ethyl 3-methyl-4-oxopentanoate (55424-74-3) → ethyl crotonate (10544-63-5)

Guidance literature:

ethyl 3-methyl-4-oxopentanoate; With aluminum oxide; N-Methyl-picolinamidrazon; In 1,4-dioxane; at 90 ℃; for 24h; Inert atmosphere;

With copper diacetate; In water; dimethyl sulfoxide; at 20 ℃; for 20h; Inert atmosphere; Glovebox; Sealed tube;

DOI:10.1021/jacs.1c09587

Reference yield:

ethyl 3-methyl-4-oxopentanoate (55424-74-3) → (2R,3S)-2,3-Dimethyl-5-oxo-tetrahydro-furan-2-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester (76405-16-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 2.) conc. HCl / 1.) benzene, toluene, -23 deg C, 80 min, 2.) methanol, -80 deg C, 1.5 h

2: 90 percent / conc. HCl / H₂O / 36 h / Heating

3: 100 percent / trimethylaluminium / CH₂Cl₂; hexane / 1.) 0 deg C, 20 min, 2.) reflux, 2 d

4: 96 percent / tetrahydrofuran / 3.5 h / Ambient temperature

5: 32 percent / tetrahydrofuran / 24 h / Ambient temperature

With hydrogenchloride; trimethylaluminum; In tetrahydrofuran; hexane; dichloromethane; water;

DOI:10.1021/ja00394a022

upstream raw materials:

ethyl 2-(bromomethyl)-2-methyl-3-oxobutanoate

Downstream raw materials:

(2R,3S)-2,3-Dimethyl-5-oxo-tetrahydro-furan-2-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester

(+)-trans-β-methyl-γ-carboxy-γ-valerolactone

ethyl crotonate