Fluoride Ion → ethyl (4-hydroxy-1H-indol-1-yl)acetate

Participants

Reaction Steps

To a solution of ethyl (4-{[tert-butyl(dimethyl)silyl]oxy}-1H-indol-1-yl)acetate (3.7 g) in THF (74 mL) was added tetra n-butylammomium fluoride (3.5 g) at ambient temperature. The reaction mixture was stirred at the same temperature for 7 hours. The resulting mixture was evaporated in vacuo and diluted with EtOAc. The organic solution was washed successively with water and brine. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=80:20-60:40) to give ethyl (4-hydroxy-1H-indol-1-yl)acetate.

Provenance & Evidence