Reaktion #1701856

Reaktionsgleichung

Ph3CCl

NEt3

2-cyanothiophene

Me3SnN3

→

titled compound

Ausbeute 80.0%

(N-triphenylmethyltetrazol-5-yl]thiophene

Ausbeute 80.0%

Lösungsmittel

CH2Cl2

Et2O EtOAc

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux under N2 for 12 hours
2. 2
   Waschenwashed with 2N HCl soln and H2O
3. 3
   TrocknenThe organic was dried over anhydrous MgSO4
4. 4
   Einengenconcentrated in vacuo
5. 5
   workup.ADDITIONThe residue, containing the free tetrazole
6. 6
   workup.DISSOLUTIONwas dissolved in CH2Cl2 (10 mL)
7. 7
   Waschenwashed with 1N NaOH, 10% citric acid and brine
8. 8
   TrocknenThe organic was dried over anhydrous MgSO4
9. 9
   Einengenconcentrated in vacuo
10. 10
    SonstigeThe product was purified by recrystallization from hexanes

Vorschrift

To a solution of 2-cyanothiophene (1.4 g; 12.8 mmol) in dry toluene (10 ml) was added Me3SnN3 (2.8 g; 13.65 mmol). The mixture was stirred at reflux under N2 for 12 hours. The reaction was cooled to room temperature diluted with CH2Cl2 and washed with 2N HCl soln and H2O. The organic was dried over anhydrous MgSO4 and concentrated in vacuo. The residue, containing the free tetrazole, was dissolved in CH2Cl2 (10 mL) and Ph3CCl (3.2 g; 0.9 equiv.) and NEt3 (3.6 mL) were added. After 20 minutes the mixture was diluted with Et2O/EtOAc and washed with 1N NaOH, 10% citric acid and brine. The organic was dried over anhydrous MgSO4 and concentrated in vacuo. The product was purified by recrystallization from hexanes. The titled compound was isolated in 80% yield, Rf=0.33 (10:1 hex/EtOAc).

Quelle