[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].N1C=CN=C1.[S:14]1[CH:18]=[CH:17][N:16]=[C:15]1[CH2:19][O:20][CH2:21][CH2:22][OH:23]>C1COCC1>[Si:5]([O:23][CH2:22][CH2:21][O:20][CH2:19][C:15]1[S:14][CH:18]=[CH:17][N:16]=1)([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:7])[CH3:6]TBDMS-Cl (2.4 g, 15.7 mmol) and imidazole (1.10 g, 16.9 mmol) were added to a sol. of 2-(thiazol-2-ylmethoxy)ethanol (2.45 g, 15.39 mmol) in THF (80 mL). The reaction mixture was stirred at rt over 15 h, partitioned between aq. sat. NH4Cl and Et2O. The phases were separated and the aq. layer was extracted with Et2O (2×). The combined org. layers were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as an orange oil (22.93 g, 87%) that was not further purified. LC-MS: tR=1.06 min, ES+: 274.24.
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