5-[(E)-2-(ethoxycarbonyl)ethenyl]-1-methoxymethyl-2-phenylsulfanyl-1H-imidazole

Base Information

• Chemical Name: 5-[(E)-2-(ethoxycarbonyl)ethenyl]-1-methoxymethyl-2-phenylsulfanyl-1H-imidazole
• CAS No.: 460990-46-9
• Molecular Formula: C₁₆H₁₈N₂O₃S
• Molecular Weight: 318.397
• Mol file: 460990-46-9.mol

Synonyms:5-[(E)-2-(ethoxycarbonyl)ethenyl]-1-methoxymethyl-2-phenylsulfanyl-1H-imidazole

Chemical Property of 5-[(E)-2-(ethoxycarbonyl)ethenyl]-1-methoxymethyl-2-phenylsulfanyl-1H-imidazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[(E)-2-(ethoxycarbonyl)ethenyl]-1-methoxymethyl-2-phenylsulfanyl-1H-imidazole

There total 2 articles about 5-[(E)-2-(ethoxycarbonyl)ethenyl]-1-methoxymethyl-2-phenylsulfanyl-1H-imidazole 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: 100.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 1-(methoxymethyl)-2-(phenylthio)-1H-imidazole-5-carbaldehyde (460990-43-6) → 5-[(E)-2-(ethoxycarbonyl)ethenyl]-1-methoxymethyl-2-phenylsulfanyl-1H-imidazole (460990-46-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In acetonitrile; at 20 ℃;

DOI:10.1016/S0040-4039(02)00782-7

Reference yield:

1-(methoxymethyl)-2-(phenylthio)-1H-imidazole (67319-05-5) → 5-[(E)-2-(ethoxycarbonyl)ethenyl]-1-methoxymethyl-2-phenylsulfanyl-1H-imidazole (460990-46-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi; 2,2,6,6-tetramethylpiperidine / tetrahydrofuran; 1,2-dimethoxy-ethane; hexane / 1 h / -78 °C

1.2: 83 percent / tetrahydrofuran; 1,2-dimethoxy-ethane; hexane / 4 h / -78 - 20 °C

2.1: 100 percent / DBU; LiCl / acetonitrile / 5 h / 0 - 20 °C

With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; acetonitrile; 2.1: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.tet.2006.08.027

Reference yield: 71.0%

5-[(E)-2-(ethoxycarbonyl)ethenyl]-1-methoxymethyl-2-phenylsulfanyl-1H-imidazole (460990-46-9) → 4-[(E)-2-(ethoxycarbonyl)ethenyl]-2-phenylsulfanyl-1H-imidazole

Guidance literature:

With hydrogenchloride; In ethanol; water; at 60 ℃;

DOI:10.1016/S0040-4039(02)00782-7

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

1-(methoxymethyl)-2-(phenylthio)-1H-imidazole-5-carbaldehyde

1-(methoxymethyl)-2-(phenylthio)-1H-imidazole