Water → HCID 21474716, compound

Participants

Reaction Steps

1.2 ml of a 1.0M solution of tetrabutyl ammonium fluoride in tetrahydrofuran were added dropwise to a solution of 152 mg of 3-(2-t-butyldimethylsilyloxy-1-methylethyl)-5-(3-chlorophenoxymethyl)oxazolidin-2-one (prepared as described in Preparation 11) in 1 ml of tetrahydrofuran, whilst ice-cooling. The mixture was then stirred at room temperature for 1.5 hours. At the end of this time, water and sodium chloride were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and then the ethyl acetate was removed from the extract by evaporation under reduced pressure. The resulting residue was purified by silica gel column chromatography, using a gradient elution method, with mixtures of ethyl acetate and ethanol in ratios ranging from 1:0 to 20:1 by volume as the eluent, to give 97 mg of the title compound having an Rf value of 0.28 (on silica gel thin layer chromatography, using ethyl acetate as the developing solvent).

Provenance & Evidence