Tetrabutylammonium Fluoride → HCID 68911470, compound

HRID 2102551Notes

Reaction equation

HRID 2102551 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-199def4f878144a89761c9070b744045
Source dataset
uspto-grants-2009_08
Patent number
US07576078B2

Reaction notes

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