C([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:11]([F:23])[CH2:10]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[Si:16]([O:15][CH:12]1[CH2:13][CH2:14][CH:9]([OH:8])[CH2:10][CH:11]1[F:23])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]To a stirred solution {[4-(benzyloxy)-2-fluorocyclohexyl]oxy}(tert-butyl)dimethylsilane (4.66 g, 13.8 mmol) in MeOH (30 mL) was added Pd(OH)2 in MeOH (20 mL). The flask was evacuated and filled with hydrogen several times, and left to stir overnight under hydrogen atmosphere. The mixture was diluted with DCM, filtered through a pad of Celite, and concentrated to afford the title compound.
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