Reaktion #979431

Reaktionsgleichung

(4-allyloxy-phenyl)-methanethiol

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

sodium hydride

→

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

Ausbeute 86.3%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added under argon at −30° C
2. 2
   SonstigeAfter quenching with 100 ml water
3. 3
   workup.ADDITIONthe mixture was diluted with dichloromethane
4. 4
   Waschenwashed with water
5. 5
   Sonstigedried
6. 6
   Sonstigeevaporated
7. 7
   SonstigePurification on silica
8. 8
   Waschenafter elution with ethyl acetate/heptane 1:1

Vorschrift

To a mixture of 13.0 g (50.5 mmol) (4-allyloxy-phenyl)-methanethiol and 13.5 g (50.5 mmol) toluene-4-sulfonic acid 2-[1,2,3]triazol-1-yl-ethyl ester in 125 ml N,N-dimethylformamide was added under argon at −30° C. 2.42 g (101 mmol) sodium hydride. The mixture was allowed to warm up to room temperature and was stirred under argon for 12 hours. After quenching with 100 ml water, the mixture was diluted with dichloromethane, washed with water, dried and evaporated. Purification on silica after elution with ethyl acetate/heptane 1:1 yielded 12.0 g (86%) 1-[2-(4-allyloxy-benzylsulfanyl)-ethyl]-1H[1,2,3]triazole as slightly yellow oil.

Quelle