Imidazole → HCID 86731309, compound

HRID 2277236Notes

Reaction equation

HRID 2277236 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][OH:12])=[N:9][CH:10]=1.N1C=CN=C1.CN(C=O)C.[C:23]([Si:27]([CH3:30])([CH3:29])Cl)([CH3:26])([CH3:25])[CH3:24]>C(OCC)(=O)C>[Si:27]([O:12][CH2:11][C:8]1[CH:7]=[CH:6][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:10][N:9]=1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 58571055[5-(Methoxymethoxy)pyridin-2-yl]methanol

Product 1

HCID 86731309HCID 86731309, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (5-(methoxymethoxy)pyridin-2-yl)methanol (8.12 g), imidazole (4.90 g) and DMF (50 mL) was added tert-butyldimethylchlorosilane (8.68 g), and the mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (13.6 g).

Workup

  1. washwashed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bd23875ffdb942ee8b1f8710b39dae94
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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