Triacetoxyperiodinane → HCID 58111889, compound

Participants

Reaction Conditions

Reaction Steps

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., was slowly added a solution of Dess-Martin periodinane (9.6 g, 22.5 mmole) in 70 mL of CH2Cl2. After stirring at 25° C. for 20 minutes, the reaction mixture was diluted with 200 mL of ether and cooled by dry-ice-acetone bath. The solid precipitant was filtered out and discarded, and the filtrate was concentrated. The residue was diluted with 100 mL of ether and cooled by dry-ice-acetone bath and the precipitate was removed by filtration. The filtrate was concentrated to give 6.2 g of 4-(5-Bromo-pyridin-3-yl)-4-oxo-butyraldehyde 2 as a pale/brown oily liquid which turned to a pale brown solid after being cooled to 0° C., which was used without further purification for next step reaction.

Provenance & Evidence