Pyridine → HCID 13362113, compound

Participants

Reaction Steps

To a solution of Collins Reagent prepared with chromium trioxide (5.6 g) and pyridine (8.86 g, 112 mmol) 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-(3-pyridyl)-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 the desired 1-(5-formylpentyl)-2-(3-pyridyl)-3-methylindole as a pale yellow oil; NMR (CDCl3) δ9.7 (t, 1H); IR (neat) 2710, 1720 cm-1.

Provenance & Evidence