Potassium Carbonate → 1-Phenyl-1H-indole-5-carbaldehyde

Beteiligte Stoffe

Reaktionsschritte

The suspension of methyl indole-5-carboxylate (4) (0.70 g, 4.82 mmol), 4-iodobenzene (0.65 mL, 5.79 mmol), K2CO3 (0.93 g, 6.75 mmol), CuO (0.04 g, 0.48 mmol) in DMF (2 mL) was refluxed for 2 days. The reaction mixture was quenched with water, followed by extraction with EtOAc (20 mL×3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure to give a yellow residue, which was purified by silica gel chromatography (EtOAc:n-hexane=1:4) to afford 6 (0.30 g). 1H NMR (500 MHz, CD3OD): δ 6.83 (d, J=3.2 Hz, 1H), 7.431-7.44 (m, 1H), 7.42 (d, J=3.1 Hz, 1H), 7.49-7.51 (m, 2H), 7.54-7.60 (m, 3H), 7.77 (dd, J=8.7, 1.1 Hz, 1H), 10.06 (s, 1H).

Herkunft & Nachweise