Reaction #927235

Reaction equation

water

water

p-toluenesulfonyl chloride

7-octyne-1-ol

→

7-octynyl-p-toluenesulfonate

Yield 85.8%

Solvents

pyridine

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.STIRRINGstirred
3. 3
   Extractionextracted with ether (500 ml)
4. 4
   WashThe ether layer was washed with cold 1N-hydrochloric acid, saturated aqueous sodium hydrogencarbonate and water
5. 5
   Dryingdried over magnesium sulfate
6. 6
   Concentrationconcentrated under reduced pressure

Procedure

To an ice-cooled solution of p-toluenesulfonyl chloride (17.4 g, 91.3 mmol) in pyridine (30 ml), 7-octyne-1-ol (9.6 g, 76.1 mmol) was added dropwise, and stirred at 5-10 ° C. for 20 hours. The reaction mixture was added with water (15 ml), stirred, then poured into water (500 ml), and extracted with ether (500 ml). The ether layer was washed with cold 1N-hydrochloric acid, saturated aqueous sodium hydrogencarbonate and water, dried over magnesium sulfate, and concentrated under reduced pressure to afford 18.3 g of 7-octynyl-p-toluenesulfonate (yield; 85.7%).

Source