Potassium Carbonate → HCID 59746918, Verbindung

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a stirred solution of 6-hydroxy-5-methoxy-2,3-dihydro-1H-inden-1-one 18a (0.01 mol, 1.78 g) in acetone (50 ml) was added potassium carbonate (0.02 mol, 2.80 g). The resulting mixture was refluxed for 2 hours. After cooling to room temperature ethyl 4-bromobutyrate was added. The reaction mixture was stirred at 60° C. for 12 h. The progress of the reaction was monitored by TLC. The reaction mixture was filtered and the precipitate was washed with acetone (15 ml×2). The combined filtrate was concentrated on rotavapor and the residue was diluted with ethyl acetate. The ethyl acetate solution was successively washed with water, saturated sodium bicarbonate (Na2HCO3), water and dried over magnesium sulfate (Mg2SO4). After evaporation of the solvent the crude product was purified by passing through a short silica gel column using 0-50% gradient of ethyl acetate and hexane as eluent to give the pure indanone as colorless thick liquid in 30% yield (0.87 g). 1H NMR (400 MHz, CDCl3): δ 1.21 (3H, broad t); 2.16 (2H, m); 2.44 (2H, m); 2.59 (2H, m); 2.96 (2H, m); 3.93 (3H, s); 4.04 (2H, broad t); 4.10 (2H, broad q); 6.84 (1H, m); 7.43 (1H, s); 7.12 (1H, s). MS (ESI): m/z=293.20 (M+H+).

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