(5-methyl-3-(pyridin-4-yl)isoxazol-4-yl)methanol(WXC04555) synthesis

Yield:1159251-58-7 65%

Reaction Conditions:

with sodium hydroxide in tetrahydrofuran;water;

Steps:

67.b b)

b) (5-Methyl-3-pyridin-4-yl-isoxazol-4-yl)-methanol To a solution of 5-methyl-3-pyridin-4-yl-isoxazole-4-carboxylic acid ethyl ester (7.1 g, 17.3 mmol) in THF (350 mL) was added at 5° C. lithium aluminum hydride (635 mg, 16.7 mmol). After stirring for 2 h at this temperature further lithium aluminum hydride (318 mg, 8.4 mmol) was added and stirred for 1 h at 5° C. Water (1.9 mL) was added carefully followed by aqueous sodium hydroxide (15%, 1.9 mL) and water (0.54 mL). The resulting suspension was stirred for 15 min at ambient temperature and filtered over Hyflo. Concentration and purification by chromatography (SiO₂, heptane:ethyl acetate=50:50 to 0:100) afforded the title compound (2.15 g, 65%) as a light yellow solid. MS: m/e=191.2 [M+H]⁺.

References:

US2009/143385,2009,A1