Hexane → HCID 59331083, compound

Participants

Reaction Steps

A one liter four-necked flask equipped with a stirrer, a nitrogen inlet tube, a reflex condenser, and a thermometer was charged with 74.69 g of 1-[9-ethyl-6-(4-fluoro-2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, 538.66 g of ethyl acetate, and 67.33 g of potassium t-butoxide, and the mixture was refluxed in a nitrogen atmosphere for 1 hour. The reaction mixture was cooled to room temperature, and the white solid thus precipitated was collected by filtration by suction and washed with 500 ml of ethyl acetate. The resulting solid was stirred in 500 ml of 2N hydrochloric acid and 1.5 liters of ethyl acetate. The organic phase was washed with water until neutral. The organic phase was separated, dried with 70 g of magnesium sulfate, and filtered by suction. The solvent was removed by evaporation to give a pale yellow solid. The solid was dissolved in 150 ml of ethyl acetate and refluxed, and 100 ml of n-hexane was added thereto, followed by cooling to room temperature for crystallization. The filtrate was dissolved in 50 ml of ethyl acetate, refluxed, and 100 ml of n-hexane was added, followed by cooling to room temperature for crystallization. The resulting crystals were combined, collected by filtration by suction, and dried under reduced pressure to give 8.52 g (21%) of white crystals, which had a melting point of 132° C. and was identified by various analyses to be β-diketone compound No. 2 having a carbazolyl group.

Provenance & Evidence