[F:1][C:2]1[C:7]([C:8](OC)=[O:9])=[C:6]([CH3:12])[C:5]([I:13])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+].[H][H]>C(OCC)C>[F:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([CH3:12])[C:5]([I:13])=[CH:4][CH:3]=1To a solution of the product from Step B (5.5 g, 18.7 mmol) in diethyl ether (20 ml) was carefully added lithium aluminum hydride (0.8 g, 18.7 mmol). The mixture was stirred at room temperature for 16 h. Saturated aqueous ammonium chloride solution was added dropwise until no hydrogen gas was being generated. A few more drops of saturated aqueous ammonium chloride solution were added and the mixture was stirred at room temperature for 30 min and filtered. The filtrated was dried over magnesium sulfate and concentrated to dryness to give the title compound as a colorless oil.
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