Hydrochloric Acid → 3-[2-(benzyloxy)phenyl]-3-hydroxy-3,5,6,7-tetrahydrocyclopenta[f]indol-2(1H)-one

Participants

Reaction Steps

Several drops of a 6 mL diethyl ether solution of 5.3 g of 2-benzyloxybromobenzene were added to a suspension of 583 mg of magnesium in 2 mL of diethyl ether under a nitrogen atmosphere to initiate the reaction, after which the rest was gradually added dropwise at a rate at which heating reflux was maintained. Upon completion of the dropping, the reaction mixture was heated and refluxed for 2 hours in an oil bath, and then cooled to room temperature. A reagent prepared as above was gradually added dropwise under ice cooling and a nitrogen atmosphere to an 11 mL tetrahydrofuran solution of 1.5 g of 1,5,6,7-tetrahydrocyclopenta[f]indol-2,3-dione. Upon completion of the dropping, the temperature was raised to room temperature, and then the reaction mixture was stirred for 16 hours at that temperature. A 1 mol/L hydrochloric acid aqueous solution was poured into the reaction solution, and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine and dried with magnesium sulfate, and the drying agent was then filtered off and the solvent was distilled off under reduced pressure. The residue was refined by column chromatography (silica gel 60, mobile phase: ethyl acetate/hexane=1/2; v/v) to obtain 1.10 g of the titled compound (colorless powder).

Provenance & Evidence