Tetrabutylammonium Fluoride → 1-(4-Hydroxybutyl)-7-methoxyquinoxalin-2(1H)-one

HRID 1846990Notes

Reaction equation

HRID 1846990 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][C:14]1=[O:25])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][C:14]1=[O:25]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 867249211-(4-{[tert-Butyl(dimethyl)silyl]oxy}butyl)-7-methoxyquinoxalin-2(1H)-one

Product 1

HCID 867249221-(4-Hydroxybutyl)-7-methoxyquinoxalin-2(1H)-oneYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(4-{[Tert-butyl(dimethyl)silyl]oxy}butyl)-7-methoxyquinoxalin-2(1H)-one (363 mg, 1.0 mmol) was dissolved in tetrahydrofuran (10.9 ml). Tetrabutyl ammonium fluoride (1M tetrahydrofuran solution; 1.1 ml, 1.1 mmol) was added to this solution and the mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate, washed with water and saturated sodium chloride solution, dried over magnesium sulfate and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to yield 247 mg (100%) of the title compound in the form of a light yellow syrup.

Workup

  1. washwashed with water and saturated sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-e5a34914679942c6ae507fae0525d356
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

Loading…