Tetrabutylammonium Fluoride → HCID 67053009, compound

HRID 2387332Notes

Reaction equation

HRID 2387332 reaction equation
[Si]([O:8][CH:9]([C:28]([F:31])([F:30])[F:29])[CH2:10][C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20]([N:23]=[CH:24][N:25]([CH3:27])[CH3:26])(=[O:22])=[O:21])([CH3:13])[CH3:12])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:27][N:25]([CH3:26])[CH:24]=[N:23][S:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:11]([CH3:12])([CH3:13])[CH2:10][CH:9]([OH:8])[C:28]([F:29])([F:30])[F:31])(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67132196HCID 67132196, compound

Product 1

HCID 67053009HCID 67053009, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a round bottom flask was added 2-[3-(tert-butyldimethylsilanyloxy)-4,4,4-trifluoro-1,1-dimethylbutyl]-N-[1-dimethylaminomethylidene]benzenesulfonamide (820 mg, 1.76 mmol) in 15 mL of dry THF, followed by the addition of a solution of 1M TBAF in THF (1.76 mL, 1.76 mmol). The reaction mixture was stirred at room temperature for 10 minutes, quenched with 100 mL of saturated aqueous sodium bicarbonate solution, and extracted with 250 mL of ethyl acetate. The organic layer was separated, washed with 100 mL of water and 100 mL of brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude mixture was purified by flash chromatography. The column was eluted with 0-40% EtOAc/hexanes to afford 381 mg (59%) of N-[1-dimethylaminomethylidene]-2-(4,4,4-trifluoro-3-hydroxy-1,1-dimethylbutyl)benzenesulfonamide. MS (ES+) m/z 367 [M+H]+.

Workup

  1. customquenched with 100 mL of saturated aqueous sodium bicarbonate solution
  2. extractionextracted with 250 mL of ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with 100 mL of water and 100 mL of brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude mixture was purified by flash chromatography
  9. washThe column was eluted with 0-40% EtOAc/hexanes

Sources & evidence

ORD record
ord-8817f816cdf44bf3b2f0c7a85253e8c6
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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