Methanol → [2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic Acid Methyl Ester

HRID 890448Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 890448
[CH3:1][C:2]1[C:7]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[N:3]=1.S(Cl)(Cl)=O.[CH3:26]O>>[CH3:26][O:10][C:9](=[O:11])[CH2:8][C:7]1[C:2]([CH3:1])=[N:3][C:4]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:21])[F:20])=[CH:14][CH:13]=2)=[CH:5][CH:6]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 21935927[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic Acid

Produkt 1

HCID 67072318[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic Acid Methyl EsterAusbeute 97,3 %

Versuchsvorschrift

A solution of 2.55 g (8.63 mmol) of [2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic acid in 25 ml of methanol was cooled to −10° C.; 1.88 ml (25.9 mmol) of thionyl chloride were added. The reaction mixture was then stirred at ambient temperature for 2 hours. Subsequently, the solution was stirred with ice water, then extracted with three portions of 50 ml of tert.-butyl methyl ether. The combined organic layers were washed with water, aqueous sodium hydrogen carbonate, brine and dried on anhydrous sodium sulfate. After evaporation of the solvent, 2.6 g (97.3%) of the title compound were obtained as light brown solid.

Aufarbeitung

  1. extractionextracted with three portions of 50 ml of tert.-butyl methyl ether
  2. washThe combined organic layers were washed with water, aqueous sodium hydrogen carbonate, brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. customAfter evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-a00a7dc5dcf94b038d325c9c2737aac9
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06995263B2

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