p-Toluenesulfonic acid → 1-(3-Methanesulfonylphenyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 413894

Reaktionsgleichung

Reaktionsgleichung von HRID 413894
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8])(=[O:4])=[O:3].[CH2:12]([O:14][C:15](=[O:29])[CH:16]([CH2:20][C:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:17](=O)[CH3:18])[CH3:13].C(N(CC)CC)C.CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C.C(Cl)(Cl)Cl>[CH2:12]([O:14][C:15]([C:16]1[CH:20]=[C:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:8]([C:7]2[CH:9]=[CH:10][CH:11]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=2)[C:17]=1[CH3:18])=[O:29])[CH3:13]

Komponenten

7

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 312893Ethyl 2-acetyl-4-oxo-4-phenylbutanoateHCID 4280293-(Methylsulphonyl)aniline

Produkt 1

HCID 101345751-(3-Methanesulfonylphenyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

3-Methylsulfonylaniline (1.4 mmol, 0.3 g), 3-oxo-2-(2-oxo-2-phenyl-ethyl)-butyric acid ethyl ester (1.4 mmol, 0.35 g), triethylamine (1.4 mmol, 0.14 g), and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. The resulting oil was resuspended in chloroform, then washed with water, 5% sodium bicarbonate, and brine. The organic layer was dried over NaSO4, then the solids were separated and the solvents removed under vacuum. The crude material was purified over silica gel to yield the named product as an oil. The structure of the compound was verified by 1H-NMR (CDCl3, ppm): 1.36 t (3H), 2.45 s (3H), 2.82 s (3H), 4.3 q (2H), and 6.8-7.2 m (9H).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux
  3. washwashed with water, 5% sodium bicarbonate, and brine
  4. dry with materialThe organic layer was dried over NaSO4
  5. customthe solids were separated
  6. customthe solvents removed under vacuum
  7. customThe crude material was purified over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-112f49d5fca64863ae250c0626d3f28f
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06569890B2

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