3,5-Dimethyl-4-vinyl-1H-pyrrole-2-carboxylic acid ethyl ester

Base Information

• Chemical Name: 3,5-Dimethyl-4-vinyl-1H-pyrrole-2-carboxylic acid ethyl ester
• CAS No.: 25894-11-5
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.246
• DSSTox Substance ID: DTXSID10180549
• Wikidata: Q83051099
• Mol file: 25894-11-5.mol

Synonyms:3,5-Dimethyl-4-vinyl-1H-pyrrole-2-carboxylic acid ethyl ester;25894-11-5;DTXSID10180549

Chemical Property of 3,5-Dimethyl-4-vinyl-1H-pyrrole-2-carboxylic acid ethyl ester

Chemical Property:

• Vapor Pressure: 0.000475mmHg at 25°C
• Boiling Point: 314.2°C at 760 mmHg
• Flash Point: 143.8°C
• Density: 1.069g/cm³
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 193.110278721
• Heavy Atom Count: 14
• Complexity: 227

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C(=C(N1)C)C=C)C

Technology Process of 3,5-Dimethyl-4-vinyl-1H-pyrrole-2-carboxylic acid ethyl ester

There total 5 articles about 3,5-Dimethyl-4-vinyl-1H-pyrrole-2-carboxylic acid ethyl ester 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: 48.0%

ethyl 4-iodo-3,5-dimethyl-1H-pyrrole-2-carboxylate (5408-08-2) + tri-n-butyl(vinyl)tin (7486-35-3) → ethyl 3,5-dimethyl-4-vinyl-1H-pyrrole-2-carboxylate (25894-11-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; In toluene; at 110 ℃; for 2h; Inert atmosphere;

DOI:10.1002/cmdc.201700063

Reference yield:

4-(1-hydroxyimino-ethyl)-3,5-dimethyl-pyrrole-2-carboxylic acid ethyl ester (5463-46-7) → ethyl 3,5-dimethyl-4-vinyl-1H-pyrrole-2-carboxylate (25894-11-5)

Guidance literature:

With 1,4-dioxane; nickel; at 130 ℃; under 147102 Torr; Hydrogenation;

DOI:10.1021/ja01236a025

Reference yield:

3,5-dimethyl-2-ethoxycarbonyl-1H-pyrrole (2199-44-2) → ethyl 3,5-dimethyl-4-vinyl-1H-pyrrole-2-carboxylate (25894-11-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium iodide; N-chloro-succinimide / N,N-dimethyl-formamide / 0 - 20 °C

2: bis-triphenylphosphine-palladium(II) chloride / toluene / 2 h / 110 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; N-chloro-succinimide; sodium iodide; In N,N-dimethyl-formamide; toluene; 2: |Stille Cross Coupling;

DOI:10.1002/cmdc.201700063

upstream raw materials:

4-(1-hydroxyimino-ethyl)-3,5-dimethyl-pyrrole-2-carboxylic acid ethyl ester

3,5-dimethyl-2-ethoxycarbonyl-1H-pyrrole

ethyl 4-iodo-3,5-dimethyl-1H-pyrrole-2-carboxylate

tri-n-butyl(vinyl)tin

Downstream raw materials:

4-(4-dimethylamino-cinnamylidene)-3,5-dimethyl-4H-pyrrole-2-carboxylic acid ethyl ester; perchlorate

ethyl 3,5-dimethyl-4-ethylpyrrole-2-carboxylate

Refernces