Reaction #710491

Reaction equation

water

sodium borohydride

ethyl (3,5-dichloropyridin-2-yl)(difluoro)acetate

HCl

→

2-(3,5-dichloropyridin-2-yl)-2,2-difluoroethanol

Solvents

ethanol

Conditions

Workup

1. 1
   ExtractionThe aequeous phase was extracted three times by 300 mL of ethyl acetate
2. 2
   Washthe organic phase was successively washed with brine, water
3. 3
   Dryingdried over magnesium sulfate
4. 4
   OtherAfter evaporation of the solvent under vacuum 8.5 g of yellow oil
5. 5
   Otherwere obtained
6. 6
   FiltrationAfter trituration in diisopropyl ether and filtration 6.8 g (80%) of 2-(3,5-dichloropyridin-2-yl)-2,2-difluoroethanol (Int-9)
7. 7
   Otherwere obtained as a white solid
8. 8
   OtherMp (melting point)=56° C. (M+1)=228

Procedure

To a solution of 10 g (37 mmol) of ethyl (3,5-dichloropyridin-2-yl)(difluoro)acetate (Int-7) in 60 mL of ethanol, were added portionwise at 0° C., 1.05 g (27.7 mmol) of sodium borohydride. The reaction mixture was stirred below 10° C. for 2 hours. 30 mL of 1 N HCl were then slowly added followed by 500 mL of water. The aequeous phase was extracted three times by 300 mL of ethyl acetate and the organic phase was successively washed with brine, water and dried over magnesium sulfate. After evaporation of the solvent under vacuum 8.5 g of yellow oil were obtained. After trituration in diisopropyl ether and filtration 6.8 g (80%) of 2-(3,5-dichloropyridin-2-yl)-2,2-difluoroethanol (Int-9) were obtained as a white solid. Mp (melting point)=56° C. (M+1)=228. 19F-NMR (235 MHz, CDCl3) δ (ppm): −105.85 (CF2).

Source