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Tetrahydrofuran → 1-[3-Hydroxy-2-(methoxymethoxy)propyl]-7-methoxyquinoxalin-2(1H)-one

HRID 1847002
Notes
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Reaction equation

HRID 1847002 reaction equation
[Si](O[C:9]1[C:10](=[O:28])[N:11]([CH2:21][CH:22]([O:24][CH2:25][O:26][CH3:27])[CH3:23])[C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[C:14]([O:19][CH3:20])[CH:13]=2)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:47]1CCCC1>ClCCl>[OH:47][CH2:23][CH:22]([O:24][CH2:25][O:26][CH3:27])[CH2:21][N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[C:14]([O:19][CH3:20])[CH:13]=2)[N:18]=[CH:9][C:10]1=[O:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 867249333-{[Tert-butyl(dimethyl)silyl]oxy}-2-(methoxymethoxy)propyl-7-methoxyquinoxalin-2(1H)-one

Product 1

HCID 867249321-[3-Hydroxy-2-(methoxymethoxy)propyl]-7-methoxyquinoxalin-2(1H)-oneYield 80%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

1-[3-{[Tert-butyl(dimethyl)silyl]oxy}-2-(methoxymethoxy)propyl-7-methoxyquinoxalin-2(1H)-one (863 mg, 2.11 mmol) was dissolved in tetrahydrofuran (10 ml). Tetrabutyl ammonium fluoride (1M tetrahydrofuran solution; 2.74 ml, 2.74 mmol) was added to this solution under cooling on ice, and the mixture was stirred for 3 hours. The reaction solution was diluted with dichloromethane and washed with saturated sodium bicarbonate water. After drying with anhydrous sodium sulfate, the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol) to yield 495 mg (80%) of the title compound in the form of a yellowish solid.

Workup

  1. temperatureunder cooling on ice
  2. washwashed with saturated sodium bicarbonate water
  3. dry with materialAfter drying with 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-ae214b1665e54ed790fd8fb882d93e83
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08952010B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes