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

HRID 1242355Notes

Reaction equation

HRID 1242355 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 and the reaction mixture was then stirred at ambient temperature for 2 hours. Subsequently, the solution was poured onto ice water, then extracted with three portions of 50 ml of tert.-butyl methyl ether. The combined organic layers were washed with water, aqueous NaHCO3-solution and brine, and dried over sodium sulfate. After evaporation of the solvents, 2.60 g of the title compound was obtained as light brown solid.

Workup

  1. additionSubsequently, the solution was poured onto ice water
  2. extractionextracted with three portions of 50 ml of tert.-butyl methyl ether
  3. washThe combined organic layers were washed with water, aqueous NaHCO3-solution and brine
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation of the solvents

Sources & evidence

ORD record
ord-f916bd2587dc470ba404d24bd41c5321
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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