(4E,6E)-ethyl 4,6-dimethyl-7-(4-nitrophenyl)hepta-4,6-dienoate

Base Information

• Chemical Name: (4E,6E)-ethyl 4,6-dimethyl-7-(4-nitrophenyl)hepta-4,6-dienoate
• CAS No.: 1440522-78-0
• Molecular Formula: C₁₇H₂₁NO₄
• Molecular Weight: 303.358
• Mol file: 1440522-78-0.mol

Synonyms:(4E,6E)-ethyl 4,6-dimethyl-7-(4-nitrophenyl)hepta-4,6-dienoate

Chemical Property of (4E,6E)-ethyl 4,6-dimethyl-7-(4-nitrophenyl)hepta-4,6-dienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4E,6E)-ethyl 4,6-dimethyl-7-(4-nitrophenyl)hepta-4,6-dienoate

There total 4 articles about (4E,6E)-ethyl 4,6-dimethyl-7-(4-nitrophenyl)hepta-4,6-dienoate 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:

(E)-2-methyl-3-(4-nitrophenyl)acrylaldehyde (58550-34-8,37524-18-8) + ethyl 4-((1-(tert-butyl)-1H-tetrazol-5-yl)sulfonyl)pentanoate → (4E,6E)-ethyl 4,6-dimethyl-7-(4-nitrophenyl)hepta-4,6-dienoate (1440522-78-0) + (4E,6Z)-ethyl 4,6-dimethyl-7-(4-nitrophenyl)hepta-4,6-dienoate (1440522-79-1)

Guidance literature:

With potassium hexamethylsilazane; In 1,2-dimethoxyethane; toluene; at -60 ℃; for 1.5h; Overall yield = 25 %; Overall yield = 79 mg; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201301322

Reference yield:

(E)-ethyl 2-methyl-3-(4-nitrophenyl)acrylate (53618-29-4,119870-80-3,65480-44-6) → (4E,6E)-ethyl 4,6-dimethyl-7-(4-nitrophenyl)hepta-4,6-dienoate (1440522-78-0) + (4E,6Z)-ethyl 4,6-dimethyl-7-(4-nitrophenyl)hepta-4,6-dienoate (1440522-79-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / diethyl ether / 0 °C / Inert atmosphere; Schlenk technique

2.1: oxalyl dichloride; dimethyl sulfoxide / Inert atmosphere; Schlenk technique

2.2: Inert atmosphere; Schlenk technique

3.1: potassium hexamethylsilazane / toluene; 1,2-dimethoxyethane / 1.5 h / -60 °C / Inert atmosphere; Schlenk technique

With oxalyl dichloride; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; In 1,2-dimethoxyethane; diethyl ether; toluene;

DOI:10.1002/anie.201301322

Reference yield:

4-nitrobenzaldehdye (555-16-8) → (4E,6E)-ethyl 4,6-dimethyl-7-(4-nitrophenyl)hepta-4,6-dienoate (1440522-78-0) + (4E,6Z)-ethyl 4,6-dimethyl-7-(4-nitrophenyl)hepta-4,6-dienoate (1440522-79-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: toluene / Reflux; Inert atmosphere; Schlenk technique

2.1: diisobutylaluminium hydride / diethyl ether / 0 °C / Inert atmosphere; Schlenk technique

3.1: oxalyl dichloride; dimethyl sulfoxide / Inert atmosphere; Schlenk technique

3.2: Inert atmosphere; Schlenk technique

4.1: potassium hexamethylsilazane / toluene; 1,2-dimethoxyethane / 1.5 h / -60 °C / Inert atmosphere; Schlenk technique

With oxalyl dichloride; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; In 1,2-dimethoxyethane; diethyl ether; toluene;

DOI:10.1002/anie.201301322

upstream raw materials:

(E)-2-methyl-3-(4-nitrophenyl)acrylaldehyde

(E)-ethyl 2-methyl-3-(4-nitrophenyl)acrylate

4-nitrobenzaldehdye

(2E)-2-methyl-3-(4-nitrophenyl)prop-2-en-1-ol

Downstream raw materials:

(4E,6E)-4,6-dimethyl-7-(4-nitrophenyl)hepta-4,6-dienoic acid