benzyl 3-(ethoxycarbonyl)-4-methyl-5-formyl-2-pyrrolecarboxylate

Base Information

• Chemical Name: benzyl 3-(ethoxycarbonyl)-4-methyl-5-formyl-2-pyrrolecarboxylate
• CAS No.: 81972-07-8
• Molecular Formula: C₁₇H₁₇NO₅
• Molecular Weight: 315.326
• Mol file: 81972-07-8.mol

Synonyms:benzyl 3-(ethoxycarbonyl)-4-methyl-5-formyl-2-pyrrolecarboxylate

Chemical Property of benzyl 3-(ethoxycarbonyl)-4-methyl-5-formyl-2-pyrrolecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 3-(ethoxycarbonyl)-4-methyl-5-formyl-2-pyrrolecarboxylate

There total 10 articles about benzyl 3-(ethoxycarbonyl)-4-methyl-5-formyl-2-pyrrolecarboxylate 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:

3,5-dimethyl-1H-pyrrole-2,4-dicarboxylic acid 2-benzyl ester 4-ethyl ester (68999-91-7) → benzyl 3-(ethoxycarbonyl)-4-methyl-5-formyl-2-pyrrolecarboxylate (81972-07-8)

Guidance literature:

Multi-step reaction with 8 steps

2: 63 percent / dicyclohexylcarbodiimide / tetrahydrofuran / 18 h / 20 °C

3: 60 percent / H₂ / 10percent Pd/C / ethanol / 3 h / 2585.7 Torr

4: 97 percent / I₂, NaHCO₃ / ethanol; H₂O / 1.5 h / 20 °C

5: 93 percent / H₂, sodium acetate / 10percent Pd/C / ethanol / 3 h / 2327.2 Torr

6: 80 percent / trifluoroacetic acid / 0.25 h / 5 °C

7: 93 percent / triethylamine / dimethylformamide / 48 h / 20 °C

With hydrogen; iodine; sodium acetate; sodium hydrogencarbonate; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00137a006

Reference yield:

ethyl acetoacetate (141-97-9) → benzyl 3-(ethoxycarbonyl)-4-methyl-5-formyl-2-pyrrolecarboxylate (81972-07-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) NaNO₂, acetic acid, 2.) Zn, acetic acid, sodium acetate / 1.) H₂O, 5 deg C, 15 h, 2.) 75 deg C, 1.5 h

3: 63 percent / dicyclohexylcarbodiimide / tetrahydrofuran / 18 h / 20 °C

4: 60 percent / H₂ / 10percent Pd/C / ethanol / 3 h / 2585.7 Torr

5: 97 percent / I₂, NaHCO₃ / ethanol; H₂O / 1.5 h / 20 °C

6: 93 percent / H₂, sodium acetate / 10percent Pd/C / ethanol / 3 h / 2327.2 Torr

7: 80 percent / trifluoroacetic acid / 0.25 h / 5 °C

8: 93 percent / triethylamine / dimethylformamide / 48 h / 20 °C

With hydrogen; iodine; sodium acetate; sodium hydrogencarbonate; acetic acid; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; zinc; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00137a006

Reference yield:

5-Iodo-4-methyl-1H-pyrrole-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester (81972-04-5) → benzyl 3-(ethoxycarbonyl)-4-methyl-5-formyl-2-pyrrolecarboxylate (81972-07-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / H₂, sodium acetate / 10percent Pd/C / ethanol / 3 h / 2327.2 Torr

2: 80 percent / trifluoroacetic acid / 0.25 h / 5 °C

3: 93 percent / triethylamine / dimethylformamide / 48 h / 20 °C

With hydrogen; sodium acetate; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00137a006

upstream raw materials:

benzyl 3-(ethoxycarbonyl)-4-methyl-2-pyrrolecarboxylate

N,N-dimethyl-formamide

3-ethoxycarbonyl-4-methylpyrrole-2-carboxylic acid

3,5-dimethyl-1H-pyrrole-2,4-dicarboxylic acid 2-benzyl ester 4-ethyl ester

Downstream raw materials:

dibenzyl 3,4'-bis(ethoxycarbonyl)-3',4-dimethyldipyrrylmethane-5,5'-dicarboxylate

benzyl 3-(ethoxycarbonyl)-4-methyl-5-(hydroxymethyl)-2-pyrrolecarboxylate