Reaction #1543044

Reaction equation

bromoacetonitrile

potassium carbonate

dimethyl 2-(cyanomethoxy)-4-(2-methylpropyl)-6-(trifluoromethyl)-3, 5-pyridine-dicarboxylate

→

dimethyl 2-hydroxy-4-(2-methylpropyl)-6-(trifluoromethyl)- 3, 5-pyridinedicarboxylate

Solvents

dimethylformamide

Conditions

Workup

1. 1
   Filtrationsuction filtered
2. 2
   workup.ADDITIONThe filtrate was diluted with 400 mL of water
3. 3
   Extractionextracted with four 50 mL portions of methylene chloride
4. 4
   DryingThe combined extracts were dried with magnesium sulfate
5. 5
   Otherthe solvent was removed by rotary evaporation

Procedure

This example illustrates the preparation of Compound 80, namely, dimethyl 2-(cyanomethoxy)-4-(2-methylpropyl)-6-(trifluoromethyl)-3, 5-pyridine-dicarboxylate. A solution of 6.38 g (0.019 mol) of dimethyl 2-hydroxy-4-(2-methylpropyl)-6-(trifluoromethyl)- 3, 5-pyridinedicarboxylate (Compound 1) in 50 mL of dimethylformamide was prepared and to it was added 7.2 g (0.06 mol) of bromoacetonitrile and 8.3 g (0.06 mol) of anhydrous potassium carbonate. The mixture was stirred at room temperature overnight then suction filtered. The filtrate was diluted with 400 mL of water and extracted with four 50 mL portions of methylene chloride. The combined extracts were dried with magnesium sulfate and the solvent was removed by rotary evaporation giving 7.09 g (98.9% yield) of a dark amber oil. Silica gel chromatography with 10% ethyl acetate, 90% cyclohexane gave 3.51 g (49%) of Compound 80 as a clear colorless oil.

Source