Reaktion #61770

Reaktionsgleichung

Water

(4-allyloxy-phenyl)-methanethiol

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

Sodium hydride

→

yellow oil

Ausbeute 79.0%

1-[2-(4-Allyloxy-benzylsulfanyl)-ethyl]-1H-[1,2,3]triazole

Ausbeute 79.0%

Lösungsmittel

N,N-dimethylformamide

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature (r.t.)
2. 2
   TrocknenThe organic phase was dried over Na2SO4, solvents
3. 3
   Sonstigeremoved
4. 4
   Sonstigethe remaining material purified by chromatography on silica gel (ethyl acetate/n-heptane 1:1)

Vorschrift

1.58 g (6.14 mmol) (4-allyloxy-phenyl)-methanethiol and 1.64 g (6.14 mmol) toluene-4-sulfonic acid 2-[1,2,3]triazol-1-yl-ethyl ester were dissolved in 15 ml N,N-dimethylformamide (DMF) and cooled to −30° C. 294 mg (12.3 mmol) 95% Sodium hydride were added, the mixture allowed to warm to room temperature (r.t.) and stirred for 12 h. 10 ml Water were added and the residue dissolved in dichloromethane. The organic phase was dried over Na2SO4, solvents removed and the remaining material purified by chromatography on silica gel (ethyl acetate/n-heptane 1:1) to yield 1.33 g (79%) yellow oil.

Quelle