Tetrabutylammonium Fluoride → HCID 59625958, compound

HRID 401726Notes

Reaction equation

HRID 401726 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[F:19][C:20]1[C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=[C:25]2[C:21]=1[CH:22]=[CH:23][N:24]2[Si](C(C)C)(C(C)C)C(C)C>C1COCC1.CCOC(C)=O>[F:19][C:20]1[C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=[C:25]2[C:21]=1[CH:22]=[CH:23][NH:24]2

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59625911HCID 59625911, compound

Product 1

HCID 59625958HCID 59625958, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

TBAF (1M solution in THF, 15.8 mmol, 15.8 mL) was added to a solution of compound 70b (7.9 mmol, 2.76 g) in THF at 0° C. After 10 min at room temperature, the reaction was diluted with EtOAc and washed with brine, saturated NaHCO3, and water. The organic layer was concentrated and purified by flash column chromatography (silica gel, 35% EtOAc/hexanes) to afford compound 70c.

Workup

  1. washwashed with brine, saturated NaHCO3, and water
  2. concentrationThe organic layer was concentrated
  3. custompurified by flash column chromatography (silica gel, 35% EtOAc/hexanes)

Sources & evidence

ORD record
ord-20105ef932b14ef48f0841307ae2c8ec
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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