Cesium carbonate → Ethyl 4-[(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate

Participants

Reaction Conditions

Reaction Steps

5,6,6a,7,8,9-Hexahydro-4H-2-phenalenylamine (0.250 g) and ethyl 4-iodobenzoate (0.360 g) were dissolved in anhydrous toluene (5 ml), the solution was added with tris(dibenzylideneacetone)dipalladium (0.024 g), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.036 g), and cesium carbonate (0.455 g), and the mixture was stirred overnight at 80° C. under an argon flow. The reaction mixture was left to cool, and then poured into ice water, and the mixture was extracted with diethyl ether. The organic layer was washed successively with 2 N aqueous hydrochloric acid, water and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:50) to obtain the title compound (0.160 g, yield: 36%). The compound was recrystallized from chloroform-n-hexane to obtain colorless needles (melting point: 154-155° C.).

Provenance & Evidence