Borane;tetrahydrofuran → (R)-Methyl 4-(4-fluoro-3-methylphenyl)-4-hydroxybutanoate

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Reaction Steps

A solution of BH3.THF (1M, 1.2 mL, 1.2 mmol) was added to 10 mL anhydrous THF followed by the dropwise addition of (S)-2-methyl-CBS-oxazaborolidine (1M, 109 μL, 0.1 mmol) in toluene at 25° C. After stirring for 5 min, methyl 4-(4-fluoro-3-methylphenyl)-4-oxobutanoate (229 mg, 1.0 mmol) was slowly added as a solution in 5 mL THF. The mixture was stirred for 30 min at room temperature and then the reaction was quenched by the careful addition of saturated aqueous ammonium chloride (10 mL). The resulting mixture was extracted with ethyl acetate (3×20 mL) and the combined organic layers washed with brine (2×10 mL) before being dried over Na2SO4. The solvents were removed under reduced pressure and the product isolated by silica gel chromatography to afford the title compound 181 mg, as an oil.

Provenance & Evidence