Tetrabutylammonium Fluoride → 4-Methylsulfanylthiophene-2-sulfonamide

HRID 6965Notes

Reaction equation

HRID 6965 reaction equation
C[Si](C)(C)[C:3]1[S:7][C:6]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:5][C:4]=1[S:12][CH3:13].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:13][S:12][C:4]1[CH:5]=[C:6]([S:8]([NH2:11])(=[O:10])=[O:9])[S:7][CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 220194765-Trimethylsilyl-4-methylsulfanylthiophene-2-sulfonamide

Product 1

HCID 220194954-Methylsulfanylthiophene-2-sulfonamideYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-trimethylsilyl-4-methylsulfanylthiophene-2-sulfonamide (660 mg, 2.34 mmol) in THF (10 mL) is added a solution of tetra-butylammonium fluoride (14.0 mL of 1 M in THF, 14.0 mmol). The reaction mixture is stirred at room temperature for 3 hr. The THF is removed under reduced pressure and the residue is dissolved in EtOAc (200 mL). The organic layer is washed with brine then dried (Na2SO4), filtered and concentrated in vacuo. The crude product is chromatographed on silica gel, eluting with Hex:EtOAc (2:1) to afford the title compound (400 mg, 82%).

Workup

  1. customThe THF is removed under reduced pressure
  2. dissolutionthe residue is dissolved in EtOAc (200 mL)
  3. washThe organic layer is washed with brine
  4. dry with materialthen dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product is chromatographed on silica gel
  8. washeluting with Hex

Sources & evidence

ORD record
ord-a67ac309ad074910a843d2a272c82903
Source dataset
uspto-grants-2006_08
Patent number
US07084170B2

Reaction notes

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