Imidazole → 2(1H)-Pyridinone, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-

HRID 2289619Notes

Reaction equation

HRID 2289619 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][NH:6][C:5](=[O:9])[CH:4]=1.[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1>CN(C=O)C.CCOC(C)=O>[Si:10]([O:1][CH2:2][C:3]1[CH:8]=[CH:7][NH:6][C:5](=[O:9])[CH:4]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 110946104-(Hydroxymethyl)pyridin-2(1H)-one

Product 1

HCID 110428222(1H)-Pyridinone, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Hydroxymethyl-1H-pyridin-2-one from Step 1 (1.3 g, 10.5 mmol) was dissolved in DMF. t-Butyl dimethylsilyl chloride (12.6 mmol, 1.9 g) and imidazole (12.6 mmol, 858 mg) were added and the reaction was stirred for 16 hours. The reaction mixture was diluted with EtOAc and washed with H2O (2x) and brine. The organic layer was dried (MgSO4), filtered and concentrated to yield a yellow oil Flash chromatography (EtOAC) yielded 4-(tert-butyldimethylsilyloxy-methyl)-1H-pyridin-2-one as an off white solid.

Workup

  1. washwashed with H2O (2x) and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto yield a yellow oil Flash chromatography (EtOAC)

Sources & evidence

ORD record
ord-dc29b60a216947a6960c93e824d181af
Source dataset
uspto-grants-2000_07
Patent number
US06093737

Reaction notes

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