Tetrabutylammonium Fluoride → HCID 15171473, compound

Participants

Reaction Steps

A lM solution (15 ml) of tetrabutylammonium fluoride in tetrahydrofuran was added dropwise to a solution of 3-dimethylaminoethyl-5-(3-t-butyldimethyl-silyloxypropyl)-2-(3-pyridyl)thiazolidin-4-one (2.6 g, 6.02 mmol) in dry tetrahydrofuran (12 ml) under cooling with ice. Then the mixture was stirred at room temperature for 2 hours to complete the reaction. Saturated aqueous NaHCO (10 ml) was added dropwise to the product mixture, and the resulting aqueous layer was extracted 6 times with ethyl acetate. The extract wad dried over MgSO4, and the solvent was removed under reduced pressure. The residual crude product was purified by medium-pressure liquid chromatography (Si-60® Art. 9385, eluent : hexane : ethanol : aqueous ammonia = 3000 : 400 : 50), giving 3-dimethylaminoethyl-5-(3-hydroxypropyl)-2-(3-pyridyl)thiazolidin-4-one (1.7 g, 88% yield).

Provenance & Evidence