Tetrabutylammonium Fluoride → HCID 59625958, compound

HRID 2365379Notes

Reaction equation

HRID 2365379 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-7904ba5da9524c12bf81b8e68e00cb99
Source dataset
uspto-grants-2014_04
Patent number
US08697684B2

Reaction notes

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