[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([OH:15])[CH:11]([F:16])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19].N1C=CN=C1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([O:15][Si:21]([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22])[CH:11]([F:16])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1To a stirred solution of 4-(benzyloxy)-2-fluorocyclohexanol (3.9 g, 17.4 mmol) in DMF (50 mL) were added TBSCl (3.93 g, 26.1 mmol) and imidazole (1.78 g, 26.1 mmol). The reaction was monitored by TLC. After completion of the reaction, the mixture was treated with sodium bicarbonate solution, and extracted with EtOAc. The combined organics were dried, concentrated, and purified by flash chromatography to afford the title compound.
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