(Z)-1-[3-ethoxy-1-(4-methoxyphenyl)prop-1-enyl]-4-methoxy-2-nitrobenzene

Base Information

• Chemical Name: (Z)-1-[3-ethoxy-1-(4-methoxyphenyl)prop-1-enyl]-4-methoxy-2-nitrobenzene
• CAS No.: 1276045-67-0
• Molecular Formula: C₁₉H₂₁NO₅
• Molecular Weight: 343.379
• Mol file: 1276045-67-0.mol

Synonyms:(Z)-1-[3-ethoxy-1-(4-methoxyphenyl)prop-1-enyl]-4-methoxy-2-nitrobenzene

Chemical Property of (Z)-1-[3-ethoxy-1-(4-methoxyphenyl)prop-1-enyl]-4-methoxy-2-nitrobenzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-1-[3-ethoxy-1-(4-methoxyphenyl)prop-1-enyl]-4-methoxy-2-nitrobenzene

There total 5 articles about (Z)-1-[3-ethoxy-1-(4-methoxyphenyl)prop-1-enyl]-4-methoxy-2-nitrobenzene 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: 80.0%

ethanol (64-17-5) + 4-(4-methoxyphenyl)prop-2-yn-1-ol (37614-59-8) + 4-bromo-3-nitroanizole (5344-78-5) → (Z)-1-[3-ethoxy-1-(4-methoxyphenyl)prop-1-enyl]-4-methoxy-2-nitrobenzene (1276045-67-0)

Guidance literature:

ethanol; 4-(4-methoxyphenyl)prop-2-yn-1-ol; With toluene-4-sulfonic acid; at 120 ℃; for 0.5h; Microwave irradiation;

With toluene-4-sulfonic acid hydrazide; at 50 ℃; for 0.25h; Microwave irradiation;

4-bromo-3-nitroanizole; With dichloro bis(acetonitrile) palladium(II); lithium tert-butoxide; XPhos; In 1,4-dioxane; at 90 ℃; for 1h; stereoselective reaction;

DOI:10.1016/j.tetlet.2010.12.093

Reference yield:

C19H24N2O4S + 1-iodo-4-methoxy-2-nitrobenzene (58755-70-7) → (Z)-1-[3-ethoxy-1-(4-methoxyphenyl)prop-1-enyl]-4-methoxy-2-nitrobenzene (1276045-67-0)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); lithium tert-butoxide; XPhos; In 1,4-dioxane; at 90 ℃; for 1h; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201101735

Reference yield:

4-(4-methoxyphenyl)prop-2-yn-1-ol (37614-59-8) → (Z)-1-[3-ethoxy-1-(4-methoxyphenyl)prop-1-enyl]-4-methoxy-2-nitrobenzene (1276045-67-0)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / 0.5 h / 120 °C / Microwave irradiation; Inert atmosphere

2: 0.25 h / 50 °C / Microwave irradiation; Inert atmosphere

3: dichloro bis(acetonitrile) palladium(II); lithium tert-butoxide; XPhos / 1,4-dioxane / 1 h / 90 °C / Inert atmosphere

With dichloro bis(acetonitrile) palladium(II); toluene-4-sulfonic acid; lithium tert-butoxide; XPhos; In 1,4-dioxane;

DOI:10.1002/ejoc.201101735

upstream raw materials:

ethanol

4-(4-methoxyphenyl)prop-2-yn-1-ol

4-bromo-3-nitroanizole

1-iodo-4-methoxy-2-nitrobenzene

Refernces

• 1、 Rasolofonjatovo, Evelia,Tréguier, Bret,Provot, Olivier,Hamze, Abdallah,Morvan, Estelle,Brion, Jean-Daniel,Alami, Mouad. "Palladium-catalyzed coupling of N-tosylhydrazones with ortho substituted aryl halides: Synthesis of 4-arylchromenes and related heterocycles". experimental part. p. 1036 - 1040. Retrieved 2011/03/20.