ethyl 1-(methoxycarbonyl)-β-oxo-3-cyclohexenebutanoate

Base Information

• Chemical Name: ethyl 1-(methoxycarbonyl)-β-oxo-3-cyclohexenebutanoate
• CAS No.: 114584-46-2
• Molecular Formula: C₁₄H₂₀O₅
• Molecular Weight: 268.31
• Mol file: 114584-46-2.mol

Synonyms:

Chemical Property of ethyl 1-(methoxycarbonyl)-β-oxo-3-cyclohexenebutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 1-(methoxycarbonyl)-β-oxo-3-cyclohexenebutanoate

There total 3 articles about ethyl 1-(methoxycarbonyl)-β-oxo-3-cyclohexenebutanoate 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:

1-(methoxycarbonyl)-3-cyclohexene-1-acetic acid (114584-31-5) → ethyl 1-(methoxycarbonyl)-β-oxo-3-cyclohexenebutanoate (114584-46-2)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride, DMF / benzene / 1.) 15 min, 2.) 45 deg C, 2 h

2: 1.) n-BuLi / 1.) THF, from -78 deg C to -5 deg C, 2.) -78 deg C, 30 min

With n-butyllithium; oxalyl dichloride; N,N-dimethyl-formamide; In benzene;

DOI:10.1021/jo00249a013

Reference yield:

methyl 1-(methoxycarbonyl)-3-cyclohexene-1-acetate (99397-97-4) → ethyl 1-(methoxycarbonyl)-β-oxo-3-cyclohexenebutanoate (114584-46-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / NaOH / methanol; H₂O / 144 h / 21 °C

2: oxalyl chloride, DMF / benzene / 1.) 15 min, 2.) 45 deg C, 2 h

3: 1.) n-BuLi / 1.) THF, from -78 deg C to -5 deg C, 2.) -78 deg C, 30 min

With sodium hydroxide; n-butyllithium; oxalyl dichloride; N,N-dimethyl-formamide; In methanol; water; benzene;

DOI:10.1021/jo00249a013

Reference yield:

Malonic acid monomethyl ester (16695-14-0) + 1-(methoxycarbonyl)-3-cyclohexene-1-acetyl chloride (114584-32-6) → ethyl 1-(methoxycarbonyl)-β-oxo-3-cyclohexenebutanoate (114584-46-2)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1.) THF, from -78 deg C to -5 deg C, 2.) -78 deg C, 30 min;

DOI:10.1021/jo00249a013

upstream raw materials:

Malonic acid monomethyl ester

1-(methoxycarbonyl)-3-cyclohexene-1-acetyl chloride

1-(methoxycarbonyl)-3-cyclohexene-1-acetic acid

methyl 1-(methoxycarbonyl)-3-cyclohexene-1-acetate