Tetrabutylammonium Fluoride → HCID 68911470, compound

HRID 969354Notes

Reaction equation

HRID 969354 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][C@@H:28]([CH3:41])[CH2:29][N:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][C:31]1=[O:40])(C(C)(C)C)(C)C>C1COCC1>[OH:26][CH2:27][C@@H:28]([CH3:41])[CH2:29][N:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][C:31]1=[O:40]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68908124HCID 68908124, compound

Product 1

HCID 68911470HCID 68911470, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1.2 g, 4.6 mmol) and (S)-1-[3-(tert-butyldimethylsilanyloxy)-2-methylpropyl]-1H-quinolin-2-one (0.31 g, 0.93 mmol) were dissolved in THF (5 mL) and stirred under an Argon atmosphere at rt overnight. The mixture was concentrated under reduced pressure and dissolved in EtOAc (30 mL). The solution was washed with water (15 mL), dried over Na2SO4, and concentrated under reduced pressure. The residue thereof was filtered through silica to give the crude title compound (0.19 g), which was used without further purification.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutiondissolved in EtOAc (30 mL)
  3. washThe solution was washed with water (15 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. filtrationThe residue thereof was filtered through silica

Sources & evidence

ORD record
ord-224bc319f43b42c287789ca772d09458
Source dataset
uspto-grants-2007_12
Patent number
US07307075B2

Reaction notes

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