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

Base Information

• Chemical Name: 1-benzyl-5-ethyl-2,4-dimethyl-1H-pyrrole-3-carboxylate
• CAS No.: 92977-40-7
• Molecular Formula: C16H19 N O2
• Molecular Weight: 257.332
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID30693121
• Wikidata: Q82622142
• Mol file: 92977-40-7.mol

Synonyms:2-Methoxy-6-fluorobenzylcyanide;DTXSID30693121;A844411;1-benzyl-5-ethyl-2,4-dimethyl-1H-pyrrole-3-carboxylate;5-ethyl-2,4-dimethyl-1-(phenylmethyl)-3-pyrrolecarboxylate;5-ethyl-2,4-dimethyl-1-(phenylmethyl)pyrrole-3-carboxylate

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

Chemical Property:

• PSA: 31.23000
• LogP: 3.32990
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 256.133753817
• Heavy Atom Count: 19
• Complexity: 306

Purity/Quality:

97% ^*data from raw suppliers

1-BENZYL-2,4-DIMETHYLPYRROLE-3-CARBOXYLIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1=C(C(=C(N1CC2=CC=CC=C2)C)C(=O)[O-])C

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

There total 6 articles about 1-benzyl-5-ethyl-2,4-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: 81.0%

N-propargylbenzylamine (1197-51-9) + Ethyl 2-butynoate (4341-76-8) → ethyl 1-benzyl-2,4-dimethyl-1H-pyrrole-3-carboxylate (92977-40-7)

Guidance literature:

With silver(I) acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 80 ℃; for 2h; regioselective reaction; Sealed tube;

DOI:10.1016/j.tet.2017.09.002

Reference yield: 80.0%

ethyl 2-[(E)-1-(benzylamino)ethylidene]-4-bromopent-4-enoate → ethyl 1-benzyl-2,4-dimethyl-1H-pyrrole-3-carboxylate (92977-40-7) + 1-benzyl-2,5-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; tert-butyl alcohol; at 80 ℃;

DOI:10.1016/S0040-4020(02)01298-X

Reference yield:

ethyl 2-acetyl-4-bromopent-4-enoate (90674-91-2) → ethyl 1-benzyl-2,4-dimethyl-1H-pyrrole-3-carboxylate (92977-40-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / p-TsOH / benzene / 10 h / Heating

2: potassium t-butoxide / dimethylsulfoxide; 2-methyl-propan-2-ol / 80 °C

With potassium tert-butylate; toluene-4-sulfonic acid; In dimethyl sulfoxide; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4020(02)01298-X

upstream raw materials:

ethyl acetoacetate

benzylamine

ethyl 2-acetyl-4-bromopent-4-enoate

N-propargylbenzylamine

Downstream raw materials:

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