Tetrabutylammonium Fluoride → 2-Fluoro-3-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)propanol

HRID 1847025Notes

Reaction equation

HRID 1847025 reaction equation
[Si]([O:18][CH2:19][CH:20]([F:35])[CH2:21][N:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([O:32][CH3:33])[CH:30]=2)[N:25]=[CH:24][C:23]1=[O:34])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(=O)(O)[O-].[Na+]>O1CCCC1>[F:35][CH:20]([CH2:19][OH:18])[CH2:21][N:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([O:32][CH3:33])[CH:30]=2)[N:25]=[CH:24][C:23]1=[O:34]

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 86585896Sodium bicarbonate waterHCID 867249521-(3-{[tert-Butyl(diphenyl)silyl]oxy}-2-fluoropropyl)-7-methoxyquinoxalin-2(1H)-one

Product 1

HCID 867249532-Fluoro-3-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)propanolYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3-{[tert-Butyl(diphenyl)silyl]oxy}-2-fluoropropyl)-7-methoxyquinoxalin-2(1H)-one (690 mg, 1.41 mmol) was dissolved in tetrahydrofuran (7 ml). Tetrabutyl ammonium fluoride (1M tetrahydrofuran solution; 1.83 ml, 1.83 mmol) was added to the solution under cooling on ice and the mixture was stirred at room temperature for 5 hours. Saturated sodium bicarbonate water was added to the reaction solution and the resultant was extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol) to yield 348 mg (98%) of the title compound in the form of a yellowish solid.

Workup

  1. temperatureunder cooling on ice
  2. extractionthe resultant was extracted with dichloromethane
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-482083773ac04392b06256bc3e1218a4
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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