Reaction #1121797

Reaction equation

1-(2-chloro-5-fluoro-pyridin-4-yl)-4,4-dimethoxy-butan-1-ol

Dess-Martin reagent

→

1-(2-chloro-5-fluoro-pyridin-4-yl)-4,4-dimethoxy-butan-1-one

Yield 89.5%

Solvents

DCM

Conditions

Workup

1. 1
   FiltrationThe precipitate is filtered
2. 2
   workup.ADDITIONWater is added to the filtrate
3. 3
   Extractionextracted with DCM
4. 4
   WashThe combined organic layers are washed with water, brine
5. 5
   Dryingdried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated down
8. 8
   OtherThe crude product is purified by chromatography (EtOAc/hexane: 5%˜20%)

Procedure

The suspension of 1-(2-chloro-5-fluoro-pyridin-4-yl)-4,4-dimethoxy-butan-1-ol (0.80 g, 3.03 mmol) and Dess-Martin reagent (1.54 g, 3.64 mmol) in DCM (20 mL) is stirred at room temperature for 3 hours. The precipitate is filtered. Water is added to the filtrate and extracted with DCM. The combined organic layers are washed with water, brine, dried over Na2SO4, filtered and concentrated down. The crude product is purified by chromatography (EtOAc/hexane: 5%˜20%) to give 1-(2-chloro-5-fluoro-pyridin-4-yl)-4,4-dimethoxy-butan-1-one (0.71 g, 89%). M/Z=262.10 [M+1]

Source