4-ethyl-3-methyl-1-[(4-methylbenzene)sulfonyl]-2-(prop-2-en-1-yl)-1H-pyrrole

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Chemical Name:4-ethyl-3-methyl-1-[(4-methylbenzene)sulfonyl]-2-(prop-2-en-1-yl)-1H-pyrrole
CAS No.:1402612-02-5
Molecular Formula:C₁₇H₂₁NO₂S
Molecular Weight:303.425
Hs Code.:

Synonyms:4-ethyl-3-methyl-1-[(4-methylbenzene)sulfonyl]-2-(prop-2-en-1-yl)-1H-pyrrole

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Chemical Property of 4-ethyl-3-methyl-1-[(4-methylbenzene)sulfonyl]-2-(prop-2-en-1-yl)-1H-pyrrole

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Technology Process of 4-ethyl-3-methyl-1-[(4-methylbenzene)sulfonyl]-2-(prop-2-en-1-yl)-1H-pyrrole

There total 3 articles about 4-ethyl-3-methyl-1-[(4-methylbenzene)sulfonyl]-2-(prop-2-en-1-yl)-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: 90.0%

: 1402612-01-4
3-ethyl-4-methyl-1-[(4-methylbenzene)sulfonyl]-1H-pyrrol-2-yl prop-2-en-1-yl carbonate

: 1402612-02-5
4-ethyl-3-methyl-1-[(4-methylbenzene)sulfonyl]-2-(prop-2-en-1-yl)-1H-pyrrole

Guidance literature:: 3-ethyl-4-methyl-1-[(4-methylbenzene)sulfonyl]-1H-pyrrol-2-yl prop-2-en-1-yl carbonate; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 20 - 180 ℃; Inert atmosphere; Microwave irradiation;

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; Inert atmosphere;

With hydrogenchloride; water; In dichloromethane; toluene; at 20 ℃; for 12h;
DOI:10.1002/anie.201202486

Reference yield:

: 766-36-9
3-ethyl-4-methyl-3-pyrrolin-2-one

: 1402612-02-5
4-ethyl-3-methyl-1-[(4-methylbenzene)sulfonyl]-2-(prop-2-en-1-yl)-1H-pyrrole

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexanes / -78 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: sodium hexamethyldisilazane / tetrahydrofuran / -60 °C / Inert atmosphere

2.2: 0.33 h / -60 °C / Inert atmosphere

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 20 - 180 °C / Inert atmosphere; Microwave irradiation

3.2: -78 °C / Inert atmosphere

3.3: 12 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium hexamethyldisilazane; In tetrahydrofuran; hexanes; toluene; 3.1: palladium-catalyzed decarboxylative allylic alkylation (PDAA) reaction (Tsuji-Trost reaction); then [3,3]-sigmatropic Cope rearrangement;
DOI:10.1002/anie.201202486

Reference yield:

: 1402612-00-3
3-ethyl-4-methyl-1-[(4-methylbenzene)sulfonyl]-2,5-dihydro-1H-pyrrol-2-one

: 1402612-02-5
4-ethyl-3-methyl-1-[(4-methylbenzene)sulfonyl]-2-(prop-2-en-1-yl)-1H-pyrrole

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / -60 °C / Inert atmosphere

1.2: 0.33 h / -60 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 20 - 180 °C / Inert atmosphere; Microwave irradiation

2.2: -78 °C / Inert atmosphere

2.3: 12 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hexamethyldisilazane; In tetrahydrofuran; toluene; 2.1: palladium-catalyzed decarboxylative allylic alkylation (PDAA) reaction (Tsuji-Trost reaction); then [3,3]-sigmatropic Cope rearrangement;
DOI:10.1002/anie.201202486