4-acetyl-5-methyl-3-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester

Base Information

• Chemical Name: 4-acetyl-5-methyl-3-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester
• CAS No.: 14533-80-3
• Molecular Formula: C₁₆H₁₇NO₃
• Molecular Weight: 271.316
• Mol file: 14533-80-3.mol

Synonyms:4-acetyl-5-methyl-3-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester

Chemical Property of 4-acetyl-5-methyl-3-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 4-acetyl-5-methyl-3-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester

There total 4 articles about 4-acetyl-5-methyl-3-phenyl-1H-pyrrole-2-carboxylic acid ethyl 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: 92.8%

ethyl 3-oxo-3-phenylpropionate (94-02-0) + acetylacetone (123-54-6,81235-32-7) → 4-acetyl-5-methyl-3-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester (14533-80-3)

Guidance literature:

ethyl 3-oxo-3-phenylpropionate; With acetic acid; sodium nitrite; In water; at 20 ℃; for 5h; Cooling with ice;

acetylacetone; With zinc; In water; at -5 - 85 ℃; for 3h;

Reference yield: 77.0%

ethyl 3-phenyl-2H-azirine-2-carboxylate (23893-63-2) + acetylacetone (123-54-6,81235-32-7) → 4-acetyl-5-methyl-3-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester (14533-80-3)

Guidance literature:

With nickel(II) chloride hexahydrate; In acetonitrile; at 20 ℃; for 24h; Reagent/catalyst;

DOI:10.1039/c5ra01889g

Reference yield:

ethyl 3-oxo-3-phenylpropionate (94-02-0) → 4-acetyl-5-methyl-3-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester (14533-80-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium nitrite / acetic acid / 72 h / 19.85 °C

2: Zn / acetic acid / 4 h / Heating

With zinc; sodium nitrite; In acetic acid;

DOI:10.1107/S0108270102018255

upstream raw materials:

ethyl bezoylacetate oxime

acetylacetone

ethyl 3-oxo-3-phenylpropionate

ethyl 3-phenyl-2H-azirine-2-carboxylate

Downstream raw materials:

1-(2-methyl-4-phenyl-1H-pyrrol-3-yl)ethan-1-one