Triethylamine → HCID 22662877, compound

HRID 1424972Notes

Reaction equation

HRID 1424972 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[CH3:8].C(N(CC)CC)C.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].C(OCC)(=O)C>CN(C=O)C>[Si:16]([O:1][CH2:2][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[CH3:8])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 1224334-hydroxymethyl-5-methyl-1H-imidazole

Product 1

HCID 22662877HCID 22662877, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(Hydroxymethyl)-5-methyl-1H-imidazole (4 g, 26.9 mmol) was dissolved in DMF (80 mL). Triethylamine (13.5 mL, 96.9 mmol) and tert-butyl(dimethyl)silyl chloride (4.68 g, 31.0 mmol) were added, followed by stirring for three hours. Ethyl acetate was added to the reaction solution, and the organic layer was washed with brine and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1, dichloromethane/methanol=92/8) to obtain 4.67 g of the title compound (77%).

Workup

  1. washthe organic layer was washed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentration under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1, dichloromethane/methanol=92/8)

Sources & evidence

ORD record
ord-a4525a76b3d844d89bc3be11d23476c7
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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