5-Formyl-2,4-dimethyl-1H-pyrrole-3-acetic acid ethyl ester

Base Information

• Chemical Name: 5-Formyl-2,4-dimethyl-1H-pyrrole-3-acetic acid ethyl ester
• CAS No.: 129689-56-1
• Molecular Formula: C₁₁H₁₅NO₃
• Molecular Weight: 209.245
• Hs Code.: 2933998090
• Mol file: 129689-56-1.mol

Synonyms:

Chemical Property of 5-Formyl-2,4-dimethyl-1H-pyrrole-3-acetic acid ethyl ester

Chemical Property:

• Boiling Point: 336℃
• Flash Point: 157℃
• PSA: 0.00000
• Density: 1.154
• LogP: 0.00000

Purity/Quality:

99% ^*data from raw suppliers

5-formyl-2,4-dimethyl-1H-Pyrrole-3-aceticacidethylester 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Formyl-2,4-dimethyl-1H-pyrrole-3-acetic acid ethyl ester

There total 6 articles about 5-Formyl-2,4-dimethyl-1H-pyrrole-3-acetic 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: 71.0%

4-ethoxycarbonylmethyl-3,5-dimethylpyrrole-2-carboxylic acid (96096-21-8) + orthoformic acid triethyl ester (122-51-0) → 4-ethoxycarbonylmethyl-3,5-dimethylpyrrole-2-carboxaldehyde (129689-56-1)

Guidance literature:

4-ethoxycarbonylmethyl-3,5-dimethylpyrrole-2-carboxylic acid; With trifluoroacetic acid; at 20 ℃; for 0.166667h;

orthoformic acid triethyl ester; at 40 ℃; Cooling with ice;

DOI:10.1016/j.bmc.2010.12.053

Reference yield:

ethyl 3-acetyl-4-oxopentanoate (18835-02-4) → 4-ethoxycarbonylmethyl-3,5-dimethylpyrrole-2-carboxaldehyde (129689-56-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetic acid / 80 °C

1.2: 70 °C / Boiling water bath

2.1: palladium 10% on activated carbon; hydrogen; triethylamine / methanol / 16 h / 20 °C / 1551.49 Torr / Inert atmosphere

3.1: trifluoroacetic acid / 0.17 h / 20 °C

3.2: 40 °C / Cooling with ice

With palladium 10% on activated carbon; hydrogen; acetic acid; triethylamine; trifluoroacetic acid; In methanol; 1.2: Knorr type reaction;

DOI:10.1016/j.bmc.2010.12.053

Reference yield:

benzyl 4-ethoxycarbonylmethyl-3,5-dimethylpyrrole-2-carboxylate (52091-12-0) → 4-ethoxycarbonylmethyl-3,5-dimethylpyrrole-2-carboxaldehyde (129689-56-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: palladium 10% on activated carbon; hydrogen; triethylamine / methanol / 16 h / 20 °C / 1551.49 Torr / Inert atmosphere

2.1: trifluoroacetic acid / 0.17 h / 20 °C

2.2: 40 °C / Cooling with ice

With palladium 10% on activated carbon; hydrogen; triethylamine; trifluoroacetic acid; In methanol;

DOI:10.1016/j.bmc.2010.12.053

upstream raw materials:

3-ethoxycarbonylmethyl-2,4-dimethylpyrrole

N,N-dimethyl-formamide

4-ethoxycarbonylmethyl-3,5-dimethylpyrrole-2-carboxylic acid

ethyl 3-acetyl-4-oxopentanoate

Downstream raw materials:

benzyl 13-(ethoxycarbonylmethyl)-3,8-diethyl-2,7,12,14-tetramethyl-5,6-dihydropyrrin-1-carboxylate hydrobromide

Refernces

• 1、 Clezy, Peter S.,Mirza, Aminul H.,Prashar, Jognandan K.. "The Chemistry of Pyrrolic Compounds. LXV Intramolecular Cyclization of Porphyrins with Acetic Acid Chains: Hydroxy Derivatives of Deoxophylloerythroaetioporphyrin (DPEP)". . p. 857 - 866. Retrieved 2007/10/02.