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]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.
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