Reaktion #61769

Reaktionsgleichung

p-toluenesulfonic acid chloride

triethylamine

2-(1H-[1,2,3]triazol-1-yl)-ethanol

HCl

→

Toluene-4-sulfonic acid 2-[1,2,3]triazol-1-yl-ethyl ester

Lösungsmittel

dichloromethane

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 10 min.
3. 3
   SonstigeThe organic phase was separated
4. 4
   Waschenwashed with sat. NaHCO3-solution and brine
5. 5
   Trocknendried over Na2SO4 and solvents
6. 6
   workup.DISTILLATIONdistilled off

Vorschrift

A solution of 12.9 g (66.3 mmol) p-toluenesulfonic acid chloride, 2.03 g (16.6 mmol) 4-(N,N-dimethylamino)-pyridine and 11.2 ml (80.2 mmol) triethylamine in 150 ml dichloromethane was cooled to −10° C. A solution of 7.50 g (66.3 mmol) 2-(1H-[1,2,3]triazol-1-yl)-ethanol in 150 ml dichloromethane was added dropwise and the mixture stirred overnight at −4° C. 170 ml Ice and 170 ml dichloromethane were added and stirring continued for 10 min. followed by addition of 3.9 ml conc. HCl. The organic phase was separated, washed with sat. NaHCO3-solution and brine, dried over Na2SO4 and solvents distilled off. Yield 15.3 g (86%) orange crystals.

Quelle