Tetrabutylammonium Fluoride → HCID 15669338, compound

HRID 1297167Notes

Reaction equation

HRID 1297167 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-dd11fad2fda148508b4ae2b459141840
Source dataset
uspto-grants-2007_07
Patent number
US07250430B2

Reaction notes

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