2-(p-toluenesulfonyl)-3-methyl-4-(2-methoxycarbonylethyl)-1H-pyrrole

Base Information

• Chemical Name: 2-(p-toluenesulfonyl)-3-methyl-4-(2-methoxycarbonylethyl)-1H-pyrrole
• CAS No.: 942294-35-1
• Molecular Formula: C₁₆H₁₉NO₄S
• Molecular Weight: 321.397
• Mol file: 942294-35-1.mol

Synonyms:2-(p-toluenesulfonyl)-3-methyl-4-(2-methoxycarbonylethyl)-1H-pyrrole

Chemical Property of 2-(p-toluenesulfonyl)-3-methyl-4-(2-methoxycarbonylethyl)-1H-pyrrole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(p-toluenesulfonyl)-3-methyl-4-(2-methoxycarbonylethyl)-1H-pyrrole

There total 3 articles about 2-(p-toluenesulfonyl)-3-methyl-4-(2-methoxycarbonylethyl)-1H-pyrrole 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: 62.0%

[(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2,36635-61-7) + Methyl 5-acetoxy-4-nitrohexanoate (100780-38-9) → 2-(p-toluenesulfonyl)-3-methyl-4-(2-methoxycarbonylethyl)-1H-pyrrole (942294-35-1)

Guidance literature:

With N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; isopropyl alcohol; at 20 ℃; for 24h;

DOI:10.1007/s00706-006-0543-8

Reference yield:

methyl 4-nitro-5-hydroxyhexanoate (87377-94-4) → 2-(p-toluenesulfonyl)-3-methyl-4-(2-methoxycarbonylethyl)-1H-pyrrole (942294-35-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / DMAP / 20 °C

2: 62 percent / 1,1,3,3-tetramethylguanidine / tetrahydrofuran; propan-2-ol / 24 h / 20 °C

With dmap; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; isopropyl alcohol; 2: Barton-Zard condensation;

DOI:10.1007/s00706-006-0543-8

Reference yield:

methyl 4-nitrobutyrate (13013-02-0) → 2-(p-toluenesulfonyl)-3-methyl-4-(2-methoxycarbonylethyl)-1H-pyrrole (942294-35-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / KF / propan-2-ol / 20 °C

2: 95 percent / DMAP / 20 °C

3: 62 percent / 1,1,3,3-tetramethylguanidine / tetrahydrofuran; propan-2-ol / 24 h / 20 °C

With dmap; potassium fluoride; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; isopropyl alcohol; 1: Henry reaction / 3: Barton-Zard condensation;

DOI:10.1007/s00706-006-0543-8

upstream raw materials:

[(p-methylphenyl)sulfonylmethyl]isonitrile

Methyl 5-acetoxy-4-nitrohexanoate

methyl 4-nitrobutyrate

methyl 4-nitro-5-hydroxyhexanoate

Downstream raw materials:

3-(2-methoxycarbonylethyl)-4-methyl-5-(p-toluenesulfonyl)-3-pyrrolin-2-one

2-(p-toluenesulfonyl)-3-methyl-4-(2-methoxycarbonylethyl)-5-bromo-1H-pyrrole