Hydrochloric Acid → 2a-(4-Pentenyl)-2a,3,4,5-tetrahydrobenzo[cd]indol-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

2a,3,4,5-Tetrahydro-1H-benz[cd]indol-2-one (4.0 g, 23 mmol) was dissolved in anhydrous N,N-dimethylformamide (100 ml), and the solution was mixed with sodium hydride (760 mg, 190 mmol) and stirred at 0° C. for 1 hour. The reaction solution was mixed with 1-bromopentene (3.8 ml, 25 mmol) and stirred at −40° C. for 2 hours. Ethyl acetate, water and hydrochloric acid (1 N) were added to the reaction solution. The reaction product was extracted with ethyl acetate, washed with saturated brine and then dried with anhydrous sodium sulfate, and the material obtained by evaporating the solvent under a reduced pressure was separated and purified by a silica gel column chromatography to obtain 2.7 g (11 mmol, 49% in yield) of the title compound.

Provenance & Evidence