Reaktion #927235

Reaktionsgleichung

water

water

p-toluenesulfonyl chloride

7-octyne-1-ol

→

7-octynyl-p-toluenesulfonate

Ausbeute 85.8%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle