Sodium Bicarbonate → ethyl (3S)-3-sulfanyl-3,6-dihydro-2H-pyran-4-carboxylate

Participants

Reaction Steps

To a solution (100 mL) of ethyl (3S)-3-(acetylsulfanyl)-3,6-dihydro-2H-pyran-4-carboxylate (19.5 g) in ethanol was added dropwise hydrochloric acid-ethanol solution (24% w/w, 100 mL) at 0° C. The reaction mixture was stirred at room temperature for 40 hr, and cooled to 0° C. Saturated aqueous sodium hydrogen carbonate solution (750 mL) was added dropwise. The reaction mixture was maintained at 10° C. or lower, and the final pH was adjusted to 7 to 8. After extraction with ethyl acetate (500 mL×2), the extract was washed with water (300 mL×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=5:1) to give the title compound (14.5 g, 91%).

Provenance & Evidence