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]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
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