Hydrochloric Acid → 5-[4-fluoro-2-(trifluoromethyl)phenyl]-4-methyl-1H-pyrrole-3-carboxylic acid

HRID 451359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 451359
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][CH:11]=[C:10]([C:13]([O:15]C)=[O:14])[C:9]=2[CH3:17])=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:3]=1.[OH-].[Na+].Cl>CO.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][CH:11]=[C:10]([C:13]([OH:15])=[O:14])[C:9]=2[CH3:17])=[C:4]([C:18]([F:21])([F:19])[F:20])[CH:3]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58488519HCID 58488519, Verbindung

Produkt 1

HCID 584885215-[4-fluoro-2-(trifluoromethyl)phenyl]-4-methyl-1H-pyrrole-3-carboxylic acidAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of methyl 5-[4-fluoro-2-(trifluoromethyl)phenyl]-4-methyl-1H-pyrrole-3-carboxylate (0.23 g, 0.77 mmol) in methanol (4.0 ml) was added 5N NaOH (3.0 ml) and the mixture was stirred at 80° C. for 2.0 h. The reaction mixture was cooled to room temperature and added 2N HCl (8.0 ml). The mixture was diluted with ethyl acetate and washed with water and brine, then dried over sodium sulfate and concentrated on a rotary evaporator. The resulting residue was purified by silica-gel column chromatography (1:1 to 1:9 hexane:ethyl acetate) to give the title compound (211 mg, 96%) as a white solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated on a rotary evaporator
  5. customThe resulting residue was purified by silica-gel column chromatography (1:1 to 1:9 hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f8e9b324c9ad494d82a786838f468ac2
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487117B2

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