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Chloromethyl Methyl Ether → 1-[3-{[tert-Butyl(dimethyl)silyl]oxy}-2-(methoxymethoxy)propyl]-7-methoxyquinoxalin-2(1H)-one

HRID 1847001
Notes
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Reaction equation

HRID 1847001 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([OH:25])[CH2:11][N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][C:13]1=[O:24])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.Cl[CH2:36][O:37][CH3:38]>ClCCl>[Si:1]([O:8][CH2:9][CH:10]([O:25][CH2:36][O:37][CH3:38])[CH2:11][N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][C:13]1=[O:24])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl Ether2×HCID 81531Diisopropylethylamine2×HCID 867249301-(3-{[tert-Butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)-7-methoxyquinoxalin-2(1H)-one

Product 1

HCID 867249311-[3-{[tert-Butyl(dimethyl)silyl]oxy}-2-(methoxymethoxy)propyl]-7-methoxyquinoxalin-2(1H)-oneYield 39%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

1-(3-{[Tert-butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)-7-methoxyquinoxalin-2(1H)-one (2.0 g, 5.49 mmol) was dissolved in dichloromethane (30 ml). N,N-Diisopropylethylamine (3.35 ml, 19.22 mmol) and chloromethylmethyl ether (1.04 ml, 13.73 mmol) were added to this solution under cooling on ice, and the mixture was stirred for 2 hours. N,N-Diisopropylethylamine (3.35 ml, 19.22 mmol) and chloromethylmethyl ether (1.04 ml, 13.73 mmol) were further added to the reaction solution and stirred for 14 hours, and the reaction solution was diluted with dichloromethane and washed with water. The organic layer was dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 863 mg (39%) of the title compound in the form of a yellow oily product.

Workup

  1. temperatureunder cooling on ice
  2. stirringstirred for 14 hours
  3. washwashed with water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-32e5f2a837cd4adba705dd1c663f42ec
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