Reaktion #86836

ord-3763840832c24d868a74ed89c2111f29

Reaktionsgleichung

[N-]=[N+]=NCc1ccccc1
benzyl azide
c1ccc(Nc2ccc(-c3ccccc3)cc2)cc1
ethyl propriolate
O=C1O[C@H]([C@@H](O)CO)C([O-])=C1O.[Na+]
sodium ascorbate
CCOC(=O)c1cn(Cc2ccccc2)nn1
ethyl 1-benzyl-1H-1,2,3-triazole-4-carboxylate
Ausbeute 24.0%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe product crystallized out

Vorschrift

A solution of benzyl azide (0.200 mL; 1.61 mmol), ethyl propriolate (0.163 mL; 1.61 mmol), copper sulfate pentahydrate (0.016 mL, 1M solution in water), sodium ascorbate (0.161 mL; solution 1M in water) in a mixture of tert-butanol (3 mL) and water (3 mL) was stirred at room temperature overnight. The reaction mixture was diluted in water and the product crystallized out to furnish 0.090 g (24%) of ethyl 1-benzyl-1H-1,2,3-triazole-4-carboxylate as white crystals.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09434722B2uspto-grants-2016_09