Ethyl 4-(2-ethoxy-2-oxoethyl)-1H-pyrrole-3-carboxylate

Base Information

• Chemical Name: Ethyl 4-(2-ethoxy-2-oxoethyl)-1H-pyrrole-3-carboxylate
• CAS No.: 184921-34-4
• Molecular Formula: C₁₁H₁₅NO₄
• Molecular Weight: 225.244
• DSSTox Substance ID: DTXSID30442459
• Nikkaji Number: J860.074K
• Wikidata: Q82259746
• Mol file: 184921-34-4.mol

Synonyms:184921-34-4;ETHYL 4-(2-ETHOXY-2-OXOETHYL)-1H-PYRROLE-3-CARBOXYLATE;DTXSID30442459;HQRMUXGEYOQXPB-UHFFFAOYSA-N;AKOS015911126;AB44638;1H-Pyrrole-3-aceticacid,4-(ethoxycarbonyl)-,ethyl ester;4-(Ethoxycarbonyl)-1H-pyrrole-3-acetic acid ethyl ester

Chemical Property of Ethyl 4-(2-ethoxy-2-oxoethyl)-1H-pyrrole-3-carboxylate

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 225.10010796
• Heavy Atom Count: 16
• Complexity: 254

Purity/Quality:

98%min ^*data from raw suppliers

ETHYL-4-(2-ETHOXY-2-OXOETHYL)-1H-PYRROLE-3-CARBOXYLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC1=CNC=C1C(=O)OCC

Technology Process of Ethyl 4-(2-ethoxy-2-oxoethyl)-1H-pyrrole-3-carboxylate

There total 3 articles about Ethyl 4-(2-ethoxy-2-oxoethyl)-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: 80.0%

(E)-diethyl glutaconate (73178-43-5) + tosylmethylisocyanate lithium → 4-Ethoxycarbonylmethyl-1H-pyrrole-3-carboxylic acid ethyl ester (184921-34-4)

Guidance literature:

In tetrahydrofuran; -70 deg C to room temperature;

DOI:10.1021/jo961987j

Reference yield: 10.0%

(E)-diethyl glutaconate (73178-43-5) → 4-Ethoxycarbonylmethyl-1H-pyrrole-3-carboxylic acid ethyl ester (184921-34-4) + (E)-4-Ethoxycarbonyl-5-ethoxycarbonylmethyl-hept-3-enedioic acid diethyl ester

Guidance literature:

With [(p-methylphenyl)sulfonylmethyl]isonitrile; sodium hydride; In diethyl ether; dimethyl sulfoxide; for 4h; Ambient temperature;

DOI:10.1016/S0040-4020(97)00469-9

Reference yield:

(E)-diethyl glutaconate (73178-43-5) + [(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2,36635-61-7) → 4-Ethoxycarbonylmethyl-1H-pyrrole-3-carboxylic acid ethyl ester (184921-34-4)

Guidance literature:

With lithium hexamethyldisilazane; Yield given. Multistep reaction; 1) THF, -78 deg C, 40 min, 2) THF, -78 deg C -> room temperature, 4 h;

DOI:10.1016/S0040-4020(97)00469-9

upstream raw materials:

(E)-diethyl glutaconate

[(p-methylphenyl)sulfonylmethyl]isonitrile

Downstream raw materials:

6-Benzyl-5-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine-3-carboxylic acid ethyl ester

5-(Benzylamino-methyl)-4-ethoxycarbonylmethyl-1H-pyrrole-3-carboxylic acid ethyl ester

5-[(E)-Benzylimino-methyl]-4-ethoxycarbonylmethyl-1H-pyrrole-3-carboxylic acid ethyl ester