Hydrochloric Acid → 4-Hydroxytetrahydro-2H-thiopyran 1,1-dioxide
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]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- concentrationThe reaction mixture was concentrated
- filtrationfiltered
- concentrationThe filtrate was concentrated
- 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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