Imidazole → HCID 68599910, compound

HRID 2246097Notes

Reaction equation

HRID 2246097 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][S:9][C:10]=1[CH2:11][OH:12])=[O:5])[CH3:2].N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C=O)C.[Cl-].[Na+].O>[Si:18]([O:12][CH2:11][C:10]1[S:9][CH:8]=[N:7][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 68599145HCID 68599145, compound

Product 1

HCID 68599910HCID 68599910, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

4-Ethoxycarbonyl-5-hydroxymethylthiazole (282 mg) was dissolved in 5 ml of DMF, 123 mg of imidazole and 250 mg of t-butyldimethylsilyl chloride were added to the solution in an argon atmosphere under ice cooling, and the mixture was stirred at room temperature for 1.5 hr. Brine was added to the reaction solution, and the mixture was extracted twice with ethyl acetate. The organic layers were combined, were washed with brine, were dried over anhydrous magnesium sulfate, were filtered, and were concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1) to give 374 mg of 5-t-butyldimethylsilyloxymethyl-4-ethoxycarbonylthiazole.

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washwere washed with brine
  3. dry with materialwere dried over anhydrous magnesium sulfate
  4. filtrationwere filtered
  5. concentrationwere concentrated under the reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-8f2e88eb155343b0994f68ac6c30c491
Source dataset
uspto-grants-2010_03
Patent number
US07687490B2

Reaction notes

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