Acetonitrile → 3-(1-Tritylimidazol-4-YL) propionaldehyde

Participants

Reaction Steps

A mixture of 1 g (2.72 mmol) of 1-(triphenylmethyl)-4-[3-hydroxypropyl]imidazole, 0.55 g (4.07 mmol; 1.5 equivalents) of morpholine oxide and 1.36 g of powdered 4 Å molecular sieve in an anhydrous mixture of acetonitrile and dichloromethane (10:4) is stirred at room temperature under nitrogen. 0.047 g (0.135 mmol; 5 mol %) of tetrapropylammonium perruthenate (VII) is added in a single portion and the mixture is stirred at room temperature for 48 hours. The reaction mixture is filtered through silica gel (preloaded with ethyl acetate) and the filtrate is evaporated under reduced pressure. The oil obtained is purified by chromatography on a column of silica gel with diethyl ether as eluent to yield 3-(1-triphenylmethyl-4-imidazolyl)propionaldehyde.

Provenance & Evidence