Hydrochloric Acid → 4-Hydroxytetrahydro-2H-thiopyran 1,1-dioxide

HRID 502295Notes

Reaction equation

HRID 502295 reaction equation
[O:1]=[S:2]1(=[O:9])[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[BH4-].[Na+].Cl>O>[O:1]=[S:2]1(=[O:9])[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2622301,1-Dioxo-tetrahydro-thiopyran-4-oneHCID 4311764Sodium borohydride

Product 1

HCID 457912554-Hydroxytetrahydro-2H-thiopyran 1,1-dioxideYield 104.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1,1-dioxo-tetrahydrothiopyran-4-one (6.3 g, 36 mmol) in H2O (55 mL) was added, in portions, sodium borohydride (720 mg, 18.9 mmol). The reaction mixture was stirred at room temperature for 30 minutes and then the pH was adjusted to 4 with aq. HCl. The reaction mixture was concentrated and suspended in acetone and filtered. The filtrate was concentrated and triturated with ether/hexane to provide 1,1-dioxo-tetrahydrothiopyran-4-ol (5.63 g, 90%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customtriturated with ether/hexane

Sources & evidence

ORD record
ord-1d34609765ef4ddba2330123799f8f0d
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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