ethyl (E)-6-(4-methylphenyl)-2-ethyl-5-methyl-3,4-dioxohex-5-enoate

Base Information

• Chemical Name: ethyl (E)-6-(4-methylphenyl)-2-ethyl-5-methyl-3,4-dioxohex-5-enoate
• CAS No.: 1392325-28-8
• Molecular Formula: C₁₈H₂₂O₄
• Molecular Weight: 302.37
• Mol file: 1392325-28-8.mol

Synonyms:ethyl (E)-6-(4-methylphenyl)-2-ethyl-5-methyl-3,4-dioxohex-5-enoate

Chemical Property of ethyl (E)-6-(4-methylphenyl)-2-ethyl-5-methyl-3,4-dioxohex-5-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (E)-6-(4-methylphenyl)-2-ethyl-5-methyl-3,4-dioxohex-5-enoate

There total 9 articles about ethyl (E)-6-(4-methylphenyl)-2-ethyl-5-methyl-3,4-dioxohex-5-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: 81.0%

C25H37NO4Si (1392325-19-7) → ethyl (E)-6-(4-methylphenyl)-2-ethyl-5-methyl-3,4-dioxohex-5-enoate (1392325-28-8)

Guidance literature:

With cesium fluoride; In N,N-dimethyl-formamide; at 0 ℃; for 0.25h; Inert atmosphere;

DOI:10.1002/anie.201201724

Reference yield:

(2E,5E)-ethyl 2-ethyl-5-methyl-4-oxo-6-(p-tolyl)-3-[[2-(trimethylsilyl)ethoxy]methoxy]hexa-2,5-dienoate → ethyl (E)-6-(4-methylphenyl)-2-ethyl-5-methyl-3,4-dioxohex-5-enoate (1392325-28-8) + C18H22O4

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 20 - 40 ℃; for 48h; Overall yield = 35%;

DOI:10.1002/anie.201500881

Reference yield:

C18H27NOSi (1228457-57-5) → ethyl (E)-6-(4-methylphenyl)-2-ethyl-5-methyl-3,4-dioxohex-5-enoate (1392325-28-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere

1.2: -78 °C / Inert atmosphere

2.1: cesium fluoride / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere

With n-butyllithium; diisopropylamine; cesium fluoride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1002/anie.201201724

upstream raw materials:

C₁₈H₂₇NOSi

C₂₅H₃₇NO₄Si

ethyl 2-(chlorocarbonyl)butanoate

monoethyl DL-ethyl-malonate