Reaktion #81246

Reaktionsgleichung

potassium t-butoxide

2-propyl-4-pivaloylimidazole-5-carbonitrile

ethyl acetate

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

→

title compound

Ausbeute 85.7%

2-Propyl-4-pivaloyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carbonitrile

Ausbeute 85.7%

Lösungsmittel

N,N-dimethylacetamide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe resulting mixture was stirred at 50° C. for 4 hours
2. 2
   Sonstigethe ethyl acetate layer was separated
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   Einengenconcentrated by evaporation under reduced pressure
5. 5
   SonstigeThe syrupy residue was purified by column chromatography through silica gel

Vorschrift

1.08 g of potassium t-butoxide was added, whilst ice-cooling, to a solution of 2.00 g of 2-propyl-4-pivaloylimidazole-5-carbonitrile (prepared as described in Preparation 41) in 20 ml of N,N-dimethylacetamide, and the resulting mixture was stirred at same temperature for 10 minutes. 6.10 g of 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide were then added to the solution, and the resulting mixture was stirred at 50° C. for 4 hours. At the end of this time, ethyl acetate and water were added to the mixture, and the ethyl acetate layer was separated, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The syrupy residue was purified by column chromatography through silica gel, using 1:3 and 1:2 by volume mixtures of ethyl acetate and hexane as the eluent, to give 5.44 g of the title compound as crystals, melting at 107°-110° C.

Quelle