Reaktion #81182

Reaktionsgleichung

4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide

potassium t-butoxide

diethyl 2-propylimidazole-4,5-dicarboxylate

→

title compound

Ausbeute 78.0%

Diethyl 2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-4,5-dicarboxylate

Ausbeute 78.0%

Lösungsmittel

N,N-dimethylacetamide

N,N-dimethylacetamide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 3 hours
2. 2
   Extraktionextracting with ethyl acetate
3. 3
   TrocknenThe extract was dried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONfreed from the solvent by distillation
5. 5
   SonstigeThe residue was purified by column chromatography through silica gel
6. 6
   workup.ADDITIONby volume mixture of hexane and ethyl acetate as the eluent

Vorschrift

0.441 g of potassium t-butoxide was added to a solution of 1.00 g of diethyl 2-propylimidazole-4,5-dicarboxylate (prepared as described in Preparation 12) in 15 ml of N,N-dimethylacetamide, and the resulting mixture was stirred at room temperature for 30 minutes. A solution of 2.19 g of 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide in 15 ml of N,N-dimethylacetamide was then added dropwise to the reaction mixture at room temperature, and the reaction mixture was stirred at room temperature for 3 hours. At the end of this time, it was diluted with water and then extracting with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then freed from the solvent by distillation. The residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 2.24 g of the title compound as an amorphous solid.

Quelle