Triethylamine → 1-(3-{[tert-Butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)-7-methoxyquinoxalin-2(1H)-one

HRID 1847000Notes

Reaction equation

HRID 1847000 reaction equation
[OH:1][CH:2]([CH2:17][OH:18])[CH2:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[N:7]=[CH:6][C:5]1=[O:16].[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[Si:19]([O:18][CH2:17][CH:2]([OH:1])[CH2:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[N:7]=[CH:6][C:5]1=[O:16])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 867249291-(2,3-Dihydroxypropyl)-7-methoxyquinoxalin-2(1H)-one

Product 1

HCID 867249301-(3-{[tert-Butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)-7-methoxyquinoxalin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

1-(2,3-Dihydroxypropyl)-7-methoxyquinoxalin-2(1H)-one (3.06 g, 12.22 mmol) was dissolved in dichloromethane (75 ml). To the solution, tert-butyldimethylsilyl chloride (2.03 g, 13.44 mmol), triethylamine (2.21 ml, 15.89 mmol) and 4-dimethylamino pyridine (299 mg, 2.44 mmol) were added under cooling on ice, and the reaction mixture was stirred for 12 hours while the temperature was rising to room temperature. The reaction solution was diluted with dichloromethane, washed with water and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol) to yield 5.29 g (quantitative) of the title compound in the form of a dark orange oily product.

Workup

  1. temperatureunder cooling on ice
  2. customwas rising to room temperature
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-e1dea7828eb840c0acac01c4467505ec
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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