Réaction #4384

Équation de réaction

Tosyl chloride

3-hydroxy-5-hexyn-2-one

triethylamine

→

3-tosyloxy-5-hexyn-2-one

Rendement 55.3%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   Lavagethe mixture was washed with water
3. 3
   Séchagedried over magnesium sulfate
4. 4
   Autreevaporated in vacuo
5. 5
   AutreThe oily residue was purified by column chromatography on silica gel (60 g)

Mode opératoire

Tosyl chloride (3.81 g) was added to a solution of 3-hydroxy-5-hexyn-2-one (2.24 g) and triethylamine (2.424 g) in methylene chloride (20 ml) under ice-cooling. After being stirred for 2.5 hours, the mixture was washed with water, dried over magnesium sulfate and evaporated in vacuo. The oily residue was purified by column chromatography on silica gel (60 g) using methylene chloride as an eluent to give an oil of 3-tosyloxy-5-hexyn-2-one (2.94 g).

Source