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

HRID 1726985Notes

Reaction equation

HRID 1726985 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

HCID 67072318[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic Acid Methyl Ester

Conditions

Temperature
-10 °C

Procedure

A solution of 2.55 g (8.63 mmol) of the above prepared [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 was 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 and brine, and dried over anhydrous sodium sulfate. After evaporation of the solvent, 2.6 g of the title compound was obtained as light brown solid.

Workup

  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 and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-10fbcf5cadb14349816de41a83633fa8
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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