3,4-dimethyl-5-[(5-oxo-dihydro-furan-2-ylidene)-phenyl-methyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 3,4-dimethyl-5-[(5-oxo-dihydro-furan-2-ylidene)-phenyl-methyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester
• CAS No.: 864682-09-7
• Molecular Formula: C₂₂H₂₅NO₄
• Molecular Weight: 367.445
• Mol file: 864682-09-7.mol

Synonyms:3,4-dimethyl-5-[(5-oxo-dihydro-furan-2-ylidene)-phenyl-methyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester

Chemical Property of 3,4-dimethyl-5-[(5-oxo-dihydro-furan-2-ylidene)-phenyl-methyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-dimethyl-5-[(5-oxo-dihydro-furan-2-ylidene)-phenyl-methyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester

There total 1 articles about 3,4-dimethyl-5-[(5-oxo-dihydro-furan-2-ylidene)-phenyl-methyl]-1H-pyrrole-2-carboxylic acid tert-butyl 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%

5-phenylpent-4-ynoic acid (3350-92-3) + 2-((tert-butyloxy)carbonyl)-5-iodo-3,4-dimethylpyrrole (86568-87-8) → 3,4-dimethyl-5-[(5-oxo-dihydro-furan-2-ylidene)-phenyl-methyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester (864682-09-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-benzyl-N,N,N-triethylammonium chloride; triethylamine; In acetonitrile; for 17h; Heating;

DOI:10.1021/jo050907l

Reference yield: 55.0%

3,4-dimethyl-5-[(5-oxo-dihydro-furan-2-ylidene)-phenyl-methyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester (864682-09-7) + methyllithium (917-54-4) → 3,4-dimethyl-5-[(5-methylene-dihydro-furan-2-ylidene)-phenyl-methyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester (864682-32-6)

Guidance literature:

methyllithium; With bis(cyclopentadienyl)titanium dichloride; In diethyl ether; toluene; at 0 ℃; for 1h;

3,4-dimethyl-5-[(5-oxo-dihydro-furan-2-ylidene)-phenyl-methyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester; With bis(cyclopentadienyl)titanium dichloride; In toluene; at 80 ℃; for 6h;

With sodium hydrogencarbonate; In methanol; toluene; at 40 ℃; for 14h;

DOI:10.1021/jo050907l

Reference yield:

3,4-dimethyl-5-[(5-oxo-dihydro-furan-2-ylidene)-phenyl-methyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester (864682-09-7) → 3,4-dimethyl-5-[(5-methyl-1H-pyrrol-2-yl)-phenyl-methyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 3 steps

1.1: TiCp₂Cl₂ / toluene; diethyl ether / 1 h / 0 °C

1.2: TiCp₂Cl₂ / toluene / 6 h / 80 °C

1.3: 55 percent / aq. NaHCO₃ / toluene; methanol / 14 h / 40 °C

2.1: 97 percent / HCl / tetrahydrofuran / 0.08 h / 20 °C

3.1: 71 percent / NH₄OAc; NEt₃ / dimethylformamide / 20 h / 55 °C

With hydrogenchloride; bis(cyclopentadienyl)titanium dichloride; ammonium acetate; triethylamine; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo050907l

upstream raw materials:

5-phenylpent-4-ynoic acid

2-((tert-butyloxy)carbonyl)-5-iodo-3,4-dimethylpyrrole

Downstream raw materials:

3,4-dimethyl-5-[(5-methylene-dihydro-furan-2-ylidene)-phenyl-methyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester

5-(2,5-dioxo-1-phenyl-hexyl)-3,4-dimethyl-1H-pyrrole-2-carboxylic acid tert-butyl ester