Tetrabutylammonium Fluoride → HCID 59625958, compound

HRID 403313Notes

Reaction equation

HRID 403313 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 mL, 15.8 mmol) was added to a solution of compound 22e (2.76 g, 7.9 mmol) in THF at 0° C. After 10 min at room temperature, the reaction was diluted with EtOAc and washed sequentially 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 22f.

Workup

  1. washwashed sequentially 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-9ec8329e928f4b29ba1921ede83b2d9e
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Reaction notes

Loading…