Réaction #73540

Équation de réaction

6-chloro-N-phenyl-N-(prop-2-en-1-yl)pyridine-3-sulfonamide

mixture ( 1/1 )

n-hexane THF

NMO

→

6-chloro-N-(2,3-dihydroxypropyl)-N-phenylpyridine-3-sulfonamide

Rendement 80.0%

Solvants

water

tBuOH

tBuOH

water

Conditions de réaction

Traitement

1. 1
   Extractionextracted with Et2O (2×100 mL)
2. 2
   Séchagedried over Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated under reduced pressure

Mode opératoire

To a solution of 1.3 g (4.2 mmol) of 6-chloro-N-phenyl-N-(prop-2-en-1-yl)pyridine-3-sulfonamide in 17 mL of a mixture (1/1) of tBuOH and water are added, at room temperature, 1.37 g (11.7 mmol) of NMO and 0.52 mL (0.04 mmol) of 2.5% OsO4 in tBuOH. Stirring is continued for 12 hours. The medium is then diluted with 200 mL of water and extracted with Et2O (2×100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. 1.14 g of 6-chloro-N-(2,3-dihydroxypropyl)-N-phenylpyridine-3-sulfonamide are obtained in the form of an oil, which is used without further purification in the following step.

Source