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

HRID 1397200Notes

Reaction equation

HRID 1397200 reaction equation
C([S:4][C@H:5]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH2:8][O:7][CH2:6]1)(=O)C.Cl.C(O)C.C(=O)([O-])O.[Na+]>C(O)C>[SH:4][C@H:5]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH2:8][O:7][CH2:6]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21887872Ethanol hydrochlorideHCID 86676957ethyl (3S)-3-(acetylsulfanyl)-3,6-dihydro-2H-pyran-4-carboxylate

Product 1

HCID 86676958ethyl (3S)-3-sulfanyl-3,6-dihydro-2H-pyran-4-carboxylateYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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%).

Workup

  1. temperaturecooled to 0° C
  2. temperatureThe reaction mixture was maintained at 10° C.
  3. extractionAfter extraction with ethyl acetate (500 mL×2)
  4. washthe extract was washed with water (300 mL×2)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0e6faa3d5334cb783d028cae8c87c78
Source dataset
uspto-grants-2014_12
Patent number
US08901171B2

Reaction notes

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