Imidazole → 2-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-oxazole

HRID 1044743Notes

Reaction equation

HRID 1044743 reaction equation
N#N.[O:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH:8]([OH:10])[CH3:9].[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1.[NH4+].[Cl-]>C1COCC1.CC(=O)OCC>[C:14]([Si:11]([CH3:13])([CH3:12])[O:10][CH:8]([C:4]1[O:3][CH:7]=[CH:6][N:5]=1)[CH3:9])([CH3:17])([CH3:16])[CH3:15]

Participants

8

Reactant 5

HCID 795ImidazoleHCID 947NitrogenHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 219427861-(Oxazol-2-yl)ethanol

Product 1

HCID 668215482-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-oxazole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), 1-oxazol-2-yl-ethanol (1.21 g, 10.71 mmol) was dissolved in dry THF (50 mL). tert-Butyldimethylsilyl chloride (3.23 g, 21.43 mmol) was added at rt followed by imidazole (1.46 g, 21.43 mmol). The reaction mixture was stirred at rt for 16 h. Sat. aq. NH4Cl (100 mL) and EA (100 mL) were added, the layers separated and the aq. layer extracted with EA (1×100 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvent removed under reduced pressure. Purification of the residue by FC (4:1 hexane-Et2O) gave the title compound as a colorless oil. TLC:rf (4:1 hexane-Et2O)=0.39. LC-MS-conditions 02: tR=1.08 min; [M+H]+=228.56.

Workup

  1. customthe layers separated
  2. extractionthe aq. layer extracted with EA (1×100 mL)
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customPurification of the residue by FC (4:1 hexane-Et2O)

Sources & evidence

ORD record
ord-74d459535c0248d6818cd8bf7204db16
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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