Sodium bis(2-methoxyethoxy)aluminiumhydride → (E)-1-(3-(Benzyloxy)phenyl)but-2-en-1-ol

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To a cold solution of sodium bis(2-methoxyethoxy)aluminum hydride (65+ wt. % in toluene) (available from Aldrich) (14.8 mL, 49.1 mmol) in ether (60 mL) was added a solution of 93.A (6.20 g, 24.6 mmol) in ether (30 mL) dropwise under nitrogen at 0° C. The mixture was stirred for 5 minutes at 0° C., the cooling bath was removed, and stirring was continued for 3 hours at room temperature. The reaction was carefully quenched at 0° C. with EtOAc, diluted with saturated aqueous Rochelle salt, and extracted with additional EtOAc. The combined organics were washed with water and brine, dried (MgSO4), and concentrated. The crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane) to afford 93.B (5.37 g, 86% yield) as a colorless oil.

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