37865-86-4

2380-86-1

74-96-4

37865-86-4

NaH (60% dispersion in oil, 0.18 g) was slowly added to a stirred solution of 1H-indol-6-ol (0.5 g) in DMF (5.0 mL) at -20 °C. After the reaction mixture was gradually warmed to room temperature, ethyl bromide (0.81 g) was added dropwise and the reaction was continued with stirring for 90 minutes. Upon completion of the reaction, the mixture was slowly poured into ice water (10 mL) and extracted with ethyl acetate. The organic layers were combined, washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure to remove the solvent. The resulting residue was purified by silica gel column chromatography using a 0-10% ethyl acetate/hexane gradient elution to afford the target product 6-ethoxy-1H-indole (0.336 g).