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

Base Information

• Chemical Name: ethyl 4-formyl-2,5-dimethyl-1H-pyrrole-3-carboxylate
• CAS No.: 776-24-9
• Molecular Formula: C10H13 N O3
• Molecular Weight: 195.218
• Mol file: 776-24-9.mol

Synonyms:Pyrrole-3-carboxylicacid, 4-formyl-2,5-dimethyl-, ethyl ester (6CI,7CI,8CI); NSC 19438

Chemical Property of ethyl 4-formyl-2,5-dimethyl-1H-pyrrole-3-carboxylate

Chemical Property:

• Vapor Pressure: 2.12E-06mmHg at 25°C
• Boiling Point: 393.5°Cat760mmHg
• Flash Point: 191.8°C
• Density: 1.173g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ethyl 4-formyl-2,5-dimethyl-1H-pyrrole-3-carboxylate

There total 7 articles about ethyl 4-formyl-2,5-dimethyl-1H-pyrrole-3-carboxylate 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: 87.0%

2,5-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester (2199-52-2) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → ethyl 4-formyl-2, 5-dimethyl-1H-pyrrole-3-carboxylate (776-24-9)

Guidance literature:

N,N-dimethyl-formamide; With trichlorophosphate; at 0 ℃; for 0.5h;

2,5-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester; In 1,2-dichloro-ethane; for 0.75h; Heating;

With sodium acetate; In 1,2-dichloro-ethane; for 0.5h; Heating;

DOI:10.1007/s00706-004-0247-x

Reference yield:

ethyl acetoacetate (141-97-9) → ethyl 4-formyl-2, 5-dimethyl-1H-pyrrole-3-carboxylate (776-24-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C

1.2: 4 h / 20 °C

2.1: acetic acid; ammonium acetate / 80 °C

3.1: trichlorophosphate / 100 °C / Inert atmosphere

With ammonium acetate; sodium hydride; acetic acid; trichlorophosphate; In tetrahydrofuran;

DOI:10.1016/j.bioorg.2018.06.004

Reference yield:

ethyl 2-acetyl-4-oxopentanoate (41892-81-3) → ethyl 4-formyl-2, 5-dimethyl-1H-pyrrole-3-carboxylate (776-24-9)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid; ammonium acetate / 80 °C

2: trichlorophosphate / 100 °C / Inert atmosphere

With ammonium acetate; acetic acid; trichlorophosphate;

DOI:10.1016/j.bioorg.2018.06.004

upstream raw materials:

2,5-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester

hydrogen cyanide

Formanilid

hydrogenchloride

Downstream raw materials:

1-chloro-5,6,7-trimethyl-6H-pyrrolo<3,4-d>pyridazinium chloride

1,2-dihydro-5,6,7-trimethyl-6H-pyrrolo<3,4-d>pyridazine-1-one

3-(4-ethoxycarbonyl-2,5-dimethyl-pyrrol-3-yl)-acrylic acid

Refernces

• 1、 Boiadjiev, Stefan E.,Lightner, David A.. "Synthesis, structure, and fluorescence of isomeric indolizinediones. Carbonyl-bridged isodipyrrinones". . p. 553 - 565. Retrieved 2007/10/03.