4-Toluenesulfonyl chloride → HCID 67118558, compound

Participants

Reaction Conditions

Reaction Steps

4-Oxothiane (2.32 g, 20.0 mmol) was dissolved in ethanol. To the solution were added hydroxylamine hydrochloride (2.78 g, 40.0 mmol) and potassium carbonate (5.52 g, 40.0 mmol), and the mixture was heated to reflux for 1 hour. Water and ethyl acetate were added to the mixture, and the mixture was extracted. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The resulting residue was dissolved in pyridine (20 mL). p-Toluenesulfonyl chloride (6.46 g, 24.0 mmol) was added at −20° C., and the mixture was stirred at −20° C. for 1 hour. Water and ethyl acetate were added to the mixture, and the mixture was extracted. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The resulting residue was dissolved in ethanol, and an ethanol solution of potassium ethoxide (4 mol/L; 15.7 mL, 40.0 mmol) was added to the solution at 0° C., then the mixture was stirred for 1 hour. After stirring the mixture at 50° C. for another 1 hour, water and ethyl acetate were added thereto, and the mixture was extracted. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate) to give 3-amino-4,4-diethoxythiopyran (2.31 g, 56%).

Provenance & Evidence