Cornforth reagent → HCID 15591370, compound

Participants

Reaction Steps

1-(5-Formylpentyl)-3-methyl-2-(3-pyridyl)indole (127 mg) is dissolved in DMF (0.66 ml) and pyridinium dichromate (298 mg) added all at once. The mixture is stirred overnight at room temperature then diluted with ether:ethyl acetate (25 ml, 4:1) and filtered. The solid is washed with hot chloroform and the combined filtrates concentrated in vacuo to yield a dark brown gum which is slurried in ether:ethyl acetate (4:1) and extracted with 0.1 N aqueous sodium hydroxide (2 ml). The aqueous extract is acidified to pH 5.5-6.0 and extracted with chloroform. The chloroform extract is dried and concentrated in vacuo yielding a yellow oil; TLC (silica gel, EtOAc:hexane 1:1) indicates the presence of the desired acid. Further purification by chromatography on silica gel using ethyl acetate:hexane (1:1) as the eluent yields the desired 1-(5-carboxypentyl)-2-(3-pyridyl)-3-methylindole of Example 3.

Provenance & Evidence