Tetrabutylammonium Fluoride → HCID 15669338, compound

HRID 6962Notes

Reaction equation

HRID 6962 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[O:12][CH3:13].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:13][O: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 220194915-Trimethylsilyl-4-methoxythiophene-2-sulfonamide

Product 1

HCID 15669338HCID 15669338, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-trimethylsilyl-4-methoxythiophene-2-sulfonamide (770 mg, 2.90 mmol) in THF (10 mL) is added a solution of tetra-butylammonium fluoride (17.4 mL of 1 M in THF, 17.4 mmol). The reaction mixture is stirred at room temperature for 2 hr. The THF is removed under reduced pressure. 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 (3:1) to afford the title compound (480 mg, 86%).

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-4011bed5f5294dad8742b47fef93d11e
Source dataset
uspto-grants-2006_08
Patent number
US07084170B2

Reaction notes

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