Reaction #710493

Reaction equation

water

1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]acetone

methyl iodide

potassium hydroxide

→

desired product

Yield 39.0%

3-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-one

Yield 39.0%

Solvents

dimethoxyethane

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   Extractionwas extracted twice with 150 mL of ethyl acetate
3. 3
   WashThe organic phase was washed twice with 100 mL of water
4. 4
   Dryingdried over magnesium sulfate
5. 5
   Concentrationconcentrated
6. 6
   OtherAfter purification on silica

Procedure

6.00 g of 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]acetone (Int-11) (27 mMol) (synthesis according to P10 and comm av.) and 5.75 g of methyl iodide (40.5 mMol) were diluted in 120 mL of dimethoxyethane. 3.03 g of potassium hydroxide were added portionwise at room temperature. After cooling, 100 mL of water were added to the reaction mixture which was extracted twice with 150 mL of ethyl acetate. The organic phase was washed twice with 100 mL of water, dried over magnesium sulfate and concentrated. After purification on silica, 0.67 g (39%) of desired product 3-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-one (Int-12) were obtained, [M+1]=252.

Source