Chloromethyl Methyl Ether → 1-[3-{[tert-Butyl(dimethyl)silyl]oxy}-2-(methoxymethoxy)propyl]-7-methoxyquinoxalin-2(1H)-one
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]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- temperatureunder cooling on ice
- stirringstirred for 14 hours
- washwashed with water
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- customthe solvent was removed under reduced pressure
- customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-32e5f2a837cd4adba705dd1c663f42ec
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952010B2
Reaction notes
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