Methanol → [2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic Acid Methyl Ester
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]=1Participants
4
Procedure
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.
Workup
- extractionextracted with three portions of 50 ml of tert.-butyl methyl ether
- washThe combined organic layers were washed with water, aqueous sodium hydrogen carbonate, brine
- dry with materialdried on anhydrous sodium sulfate
- customAfter evaporation of the solvent
Sources & evidence
- ORD record
- ord-a00a7dc5dcf94b038d325c9c2737aac9
- Source dataset
- uspto-grants-2006_02
- Patent number
- US06995263B2
Reaction notes
Loading…