Reaction #417927

Reaction equation

ethylacetate cyclohexane

thioacetic acid S-(2-trifluoromethyl-benzyl)ester

methanol

3-Bromomethyl-pyridine-2-carboxylic acid methyl ester

→

colorless crystals

Yield 100.0%

3-(2-Trifluoromethyl-benzylsulfanylmethyl)-pyridine-2-carboxylic acid methyl ester

Yield 100.0%

Solvents

water

Conditions

Workup

1. 1
   Temperatureafter refluxing for 150 min the solution
2. 2
   Extractionextracted with ethylacetate
3. 3
   Dryingthe organic phase dried with sodium sulfate
4. 4
   Concentrationconcentrated

Procedure

To a solution of thioacetic acid S-(2-trifluoromethyl-benzyl)ester (10.2 g, 37.5 mmol) in methanol (130 ml) potassium carbonate (5.18 g, 37.5 mmol) was added at room temperature and it was stirred for 30 min. 3-Bromomethyl-pyridine-2-carboxylic acid methyl ester (4.40 g, 18.7 mmol) was added and after refluxing for 150 min the solution was diluted with water, extracted with ethylacetate, the organic phase dried with sodium sulfate and concentrated. Chromatography over silica with ethylacetate/cyclohexane gave 7.82 g colorless crystals (18.7 mmol).

Source