Reaction #1121786

Reaction equation

1-(5-bromo-pyridin-3-yl)-4-hydroxy-butan-1-one

1-(5-Bromo-pyridin-3-yl)-4-hydroxy-butan-1-one

Dess-Martin periodinane

→

4-(5-Bromo-pyridin-3-yl)-4-oxo-butyraldehyde

Yield 124.9%

Solvents

CH2Cl2

CH2Cl2

ether

Conditions

Workup

1. 1
   Otherof white precipitates
2. 2
   Temperaturecooled by dry-ice-acetone bath
3. 3
   FiltrationThe solid is filtered out and
4. 4
   ConcentrationThe filtrate is concentrated
5. 5
   workup.ADDITIONThe residue is diluted with 100 mL of ether
6. 6
   Temperaturecooled by dry-ice-acetone bath
7. 7
   Otherprecipitates
8. 8
   Otherwas removed by filtration
9. 9
   ConcentrationThe filtrate is concentrated

Procedure

To a solution of 1-(5-bromo-pyridin-3-yl)-4-hydroxy-butan-1-one (1) (5.0 g, 20.5 mmole) in 90 mL of CH2Cl2 at 25° C., is added a solution of Dess-Martin periodinane (9.6 g, 22.5 mmole) in 70 mL of CH2Cl2 slowly. After stirring at 25° C. for 20 minutes, the reaction mixture is diluted with 200 mL of ether (a lot of white precipitates came out of the solution) and cooled by dry-ice-acetone bath. The solid is filtered out and discarded. The filtrate is concentrated. The residue is diluted with 100 mL of ether and cooled by dry-ice-acetone bath and precipitates was removed by filtration. The filtrate is concentrated to give 6.2 g of 4-(5-Bromo-pyridin-3-yl)-4-oxo-butyraldehyde (2) as a pale brown oil which turned to a pale brown solid after cooled to 0° C., without further purification for next step reaction.

Source