Pyridine → 1-(5-Formylpentyl)-2-(1-imidazolyl)-3-methylindole

Participants

Reaction Steps

To a solution of Collins Reagent prepared with chromium trioxide (5.6 g) and pyridine (8.86 g) in dichloromethane (150 ml) at 0°-5° under a nitrogen atmosphere is added all at once 1.8 g of 1-(6-hydroxyhexyl)-3-methyl-2-(1-imidazolyl)-indole in dichloromethane (15 ml). The mixture is stirred for an additional 25 minutes, then filtered through celite. The filtrate is then passed through a silica gel column. The product is eluted from the silica gel with a 1:1 mixture of ethyl acetate:dichloromethane (500 ml). Concentration in vacuo yields 1-(5-formylpentyl)-2-(1-imidazolyl)-3-methylindole.

Provenance & Evidence