1-[1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]but-2-en-1-one

Base Information

• Chemical Name: 1-[1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]but-2-en-1-one
• CAS No.: 626232-62-0
• Molecular Formula: C₁₅H₁₇NO₃S
• Molecular Weight: 291.371
• Mol file: 626232-62-0.mol

Synonyms:1-[1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]but-2-en-1-one

Chemical Property of 1-[1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]but-2-en-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]but-2-en-1-one

There total 4 articles about 1-[1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]but-2-en-1-one 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: 91.0%

N-methoxy-N-methyl-1-tosyl-4,5-dihydro-1H-pyrrole-2-carboxamide (1009637-17-5) + allylmagnesium bromide (1730-25-2) → 1-[1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]but-2-en-1-one (626232-62-0)

Guidance literature:

In tetrahydrofuran; at -78 ℃;

DOI:10.1021/jo7024898

Reference yield: 84.0%

5-(1-ethoxybuta-1,3-dienyl)-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole (626232-61-9) → 1-[1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]but-2-en-1-one (626232-62-0)

Guidance literature:

With Amberlyst 15; In chloroform; at 25 ℃; for 20h;

DOI:10.1021/jo034939p

Reference yield:

N-tosylpyrrolidinone (10019-95-1) → 1-[1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]but-2-en-1-one (626232-62-0)

Guidance literature:

Multi-step reaction with 3 steps

1: KHMDS / toluene; tetrahydrofuran / 1 h / -78 °C

2: 54 percent / Na₂CO₃ / (PPh₃)2PdCl₂ / tetrahydrofuran; H₂O / 2.5 h / 50 °C

3: 84 percent / Amberlyst 15 / CHCl₃ / 20 h / 25 °C

With Amberlyst 15; potassium hexamethylsilazane; sodium carbonate; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; chloroform; water; toluene;

DOI:10.1021/jo034939p

upstream raw materials:

5-(1-ethoxybuta-1,3-dienyl)-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole

N-tosylpyrrolidinone

trifluoromethanesulfonic acid 1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl ester

N-methoxy-N-methyl-1-tosyl-4,5-dihydro-1H-pyrrole-2-carboxamide