HCID 10401484, compound → 6-(4-Dimethylamino-benzenesulfinyl)-hexanoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(4-dimethylamino-phenylsulfanyl)-hexanoic acid methyl ester (1.4 g, 5.0 mmol) in methanol (60 mL) was added dropwise at 0° C. a solution of sodium metaperiodate (1.3 g, 6.0 mmol) in distilled water (20 mL). The mixture was heated at 60° C. for 1 hour. The solution was concentrated under reduced pressure to give an oil that was dissolved in ethyl acetate (150 mL). The organic layer was washed with saturated aqueous sodium hydrogen carbonate (100 mL), distilled water (2×50 mL), and lastly with brine (2×50 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give an oil that was purified by flash chromatography (100:1 ethyl acetate:triethylamine) to give the title compound (1.2 g, 81%) as a colourless oil.

Provenance & Evidence