Ethyl Acetate → HCID 89975795, compound

HRID 1508668Notes

Reaction equation

HRID 1508668 reaction equation
[SH2:1].[Na].CS(O[CH:8]([CH2:10][CH:11]([S:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[CH:12]=[O:13])[CH3:9])(=O)=O.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:9][CH:8]1[S:1][CH:12]([OH:13])[CH:11]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 86586439Sodium hydrogen sulphideHCID 118108867HCID 118108867, compound

Product 1

HCID 89975795HCID 89975795, compoundYield 25,456.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.74 g of sodium hydrogen sulfide (Wako Pure Chemical Industries, Ltd.) was added to a solution of 0.60 mg of 5-oxo-4-(pyridin-2-ylsulfanyl)pentan-2-yl methanesulfonate in 10 mL of N,N-dimethylformamide at a temperature of 0° C. to 10° C., and the obtained mixture was then stirred at the same temperature as described above for 1.5 hours. Thereafter, 30 mL of ethyl acetate and 30 mL of a saturated sodium hydrogen carbonate aqueous solution were added to the reaction mixture, and the water layer was then removed. The organic layer was successively washed with 30 mL of water and a saturated sodium chloride aqueous solution, and was then dried over anhydrous magnesium sulfate. After that, the solvent was distilled away under reduced pressure. The obtained residue was purified by column chromatography (hexane/ethyl acetate=5/1), so as to obtain 120 mg of 5-methyl-3-(pyridin-2-ylsulfanyl)thiolan-2-ol in the form of a light yellow oily product.

Workup

  1. customas described above for 1.5 hours
  2. customthe water layer was then removed
  3. washThe organic layer was successively washed with 30 mL of water
  4. dry with materiala saturated sodium chloride aqueous solution, and was then dried over anhydrous magnesium sulfate
  5. distillationAfter that, the solvent was distilled away under reduced pressure
  6. customThe obtained residue was purified by column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-e86ea1631f684e7398e9db7043c483f1
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

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