1018297-63-6

GENERAL STEPS: To a suspension of LiAlH4 (75.9 mg, 2.0 mmol) in THF (2 mL) was added a solution of ethyl 3-(4-fluorophenyl)-5-methylisoxazole-4-carboxylate (0.50 g, 2.0 mmol) in THF (3 mL) dropwise over a period of 15 min at 0-10 °C. The reaction mixture was gradually warmed up to room temperature and stirred continuously at this temperature for at least 1 hour. Upon completion of the reaction, the reaction was quenched by the slow addition of water (15 mL), the resulting suspension was filtered and the filter cake was washed with ethyl acetate (15 mL). The organic and aqueous layers of the filtrate were separated and the organic layer was washed once with water (15 mL). The aqueous layers were combined and back-extracted with ethyl acetate (2 x 15 mL). All organic layers were combined, dried with anhydrous Na2SO4 and subsequently concentrated to dryness under reduced pressure at 45 °C/25 mbar to give 0.375 g (90% yield) of 3-(4-fluorophenyl)-5-methyl-4-isoxazole methanol as a light yellow solid, and HPLC analysis showed 100% purity.

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