Reaction #4384

Reaction equation

Tosyl chloride

3-hydroxy-5-hexyn-2-one

triethylamine

→

3-tosyloxy-5-hexyn-2-one

Yield 55.3%

Solvents

methylene chloride

Conditions

Workup

1. 1
   Temperaturecooling
2. 2
   Washthe mixture was washed with water
3. 3
   Dryingdried over magnesium sulfate
4. 4
   Otherevaporated in vacuo
5. 5
   OtherThe oily residue was purified by column chromatography on silica gel (60 g)

Procedure

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