4-Toluenesulfonyl chloride → 1,1-dioxidotetrahydro-2H-thiopyran-4-yl 4-methylbenzenesulfonate

HRID 502296Notes

Reaction equation

HRID 502296 reaction equation
[O:1]=[S:2]1(=[O:9])[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1.[S:10](Cl)([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)(=[O:12])=[O:11]>N1C=CC=CC=1>[S:10]([O:8][CH:5]1[CH2:6][CH2:7][S:2](=[O:9])(=[O:1])[CH2:3][CH2:4]1)([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 457912554-Hydroxytetrahydro-2H-thiopyran 1,1-dioxide

Product 1

HCID 594258721,1-dioxidotetrahydro-2H-thiopyran-4-yl 4-methylbenzenesulfonateYield 53.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1,1-Dioxo-tetrahydrothiopyran-4-ol (1.0 g, 6.6 mmol), pyridine (10 mL), and tosyl chloride (1.6 g, 8.4 mmol) were combined and stirred at room temperature overnight. The reaction mixture was concentrated, diluted in EtOAc and washed with aqueous HCl and brine. The organic layer was dried, concentrated and triturated with hexane to yield O-tosyl-1,1-dioxo-tetrahydrothiopyran-4-ol (1.073 g, 53%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted in EtOAc
  3. washwashed with aqueous HCl and brine
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customtriturated with hexane

Sources & evidence

ORD record
ord-5b11031fcffd4d2386015be456902ef3
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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