Reacción #927235

Ecuación de reacción

water

water

p-toluenesulfonyl chloride

7-octyne-1-ol

→

7-octynyl-p-toluenesulfonate

Rendimiento 85.8%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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%).

Fuente