Sodium Hydroxide → (2s)-2-(Biphenyl-4-yloxy)-3-methylbutan-1-ol

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Reaction Steps

A solution of lithium aluminium hydride (1.0M in tetrahydrofuran, 16 ml,) was added dropwise to a stirred (2S)-2-(biphenyl-4-yloxy)-3-methylbutyric acid, methyl ester (4.0 g, Example 8a)) in dry tetrahydrofuran (80 ml) at room temperature and the reaction was left to stir overnight. Water (0.6 ml), then aqueous sodium hydroxide (50%, 0.6 ml) then water (2.4 ml) were cautiously added to the solution at 0° C. Diethyl ether (200 ml) and anhydrous magnesium sulfate (10 g) were added and the solution stirred at room temperature for 10 minutes. The solution was filtered and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with dichloromethane then dichloromethane:ether (49:1) to give the sub-title compound as an oil which solidified on standing (3.43 g).

Provenance & Evidence