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

HRID 42827Notes

Reaction equation

HRID 42827 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>[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

7

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 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), 1-oxazol-2-yl-ethanol (348 mg, 3.08 mmol) was dissolved in dry THF (15 mL). tert-Butyldimethylsilyl chloride (580 mg, 3.85 mmol) was added at rt followed by imidazole (262 mg, 3.85 mmol). The reaction mixture was stirred at rt for 16 h. Sat. aq. NH4Cl (20 mL) was added, the layers separated and the aq. layer extracted with EA (2×20 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvent removed under reduced pressure. Purification of the residue by FC (1:4 Et2O-hexane) gave the title compound as a colorless oil. TLC:rf (1:4 Et2O-hexane)=0.39. LC-MS-conditions 02: tR=1.08 min, [M+H]+=228.48

Workup

  1. customthe layers separated
  2. extractionthe aq. layer extracted with EA (2×20 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 (1:4 Et2O-hexane)

Sources & evidence

ORD record
ord-fa383d1a4c1b4a2dba9e4c72e3afc6dd
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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