Tetrabutylammonium Fluoride → (6-Hydroxy-indol-1-yl)-acetic acid ethyl ester

Participants

Reaction Steps

To an ice cold solution of [6-(tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid ethyl ester (1.15 g, 3.45 mmol) in THF (11.5 ml) was added a 1 M solution of tetrabutylammonium fluoride in THF (3.45 ml, 3.45 mmol) within 15 min. The reaction mixture was stirred for 1 h at ambient temperature, poured onto 1 N HCl/ice water 1/1 and extracted two times with ethyl acetate. The combined organic layers were washed with brine/ice water 1/1 and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, heptane/AcOEt) to give 590 mg (2.7 mmol, 78%) of the title compound as colorless crystals.

Provenance & Evidence