Water → 5-(prop-2-en-1-yloxy)-1H-indole

Participants

Reaction Steps

To a suspension of 5-hydroxyindole (1.23 g, 9.24 mmol) and cesium carbonate (3.01 g, 9.24 mmol) in DMF (40 mL) under nitrogen atmosphere at 0° C. was added allylbromide (879 μl, 10.16 mmol). The reaction mixture was stirred at RT for 2 h and poured into water and extracted with EtOAc (×3). The combined organic layers were washed twice with water, dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 9:1) to give the desired compound. TLC, Rf (c-hexane/EtOAc 1:1)=0.76; tR (conditions a): 3.46 min.

Provenance & Evidence