Toluene → HCID 59321562, compound

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Reaction Steps

A solution of methyl 3-(2,4-dichloro-3-pyridinyl)-5-(1-methylethyl)-4-isoxazolecarboxylate (1.32 g, 4.2 mmol) in THF (11.7 mL) was stirred at a 0° C. as a 1.5 M solution of diisopropylaluminum hydride in toluene (9 mL, 13.4 mmol) was added; the solution was allowed to warm to room temperature and stirred overnight. A 10% aqueous solution of Rochelle's salt was added and the solution was then allowed to stir for three hours. The layers were separated and the organic layer was washed with brine. The organic layer was dried with MgSO4, filtered and concentrated. The residue was purified by chromatography (silica gel, hexane to ethyl acetate gradient elution) to yield [3-(2,4-dichloro-3-pyridinyl)-5-(1-methylethyl)-4-isoxazolyl]methanol (1.20 g, 94% 0.2 ethyl acetate). 1H NMR (400 MHz, DMSO-d6): δ 8.52 (d, J=5 Hz, 1H), 7.78 (d, J=5 Hz, 1H), 4.94 (t, J=5 Hz, 1H), 4.20 (d, J=5 Hz, 2H), 3.34 (septet, J=7 Hz, overlapping water), 1.29 (d, J=7 Hz, 6H).

Provenance & Evidence