[C:1]([C:5]1[O:6][C:7]([CH3:14])=[C:8]([C:10]([O:12]C)=[O:11])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].Cl>C1COCC1.O>[C:1]([C:5]1[O:6][C:7]([CH3:14])=[C:8]([C:10]([OH:12])=[O:11])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]A mixture of methyl 2-tert-butyl-5-methyloxazole-4-carboxylate (44 mg, 0.22 mmol) and lithium hydroxide hydrate (47 mg, 1.1 mmol) in THF (1 mL) and water (1 mL) was stirred at room temperature for 19 hours. To the reaction was added 1 M HCl(aq) (1.1 mL, 1.1 mmol) and water, and the reaction was extracted with ethyl acetate. The combined extracts were washed with water, dried over sodium sulfate, and evaporated to give 2-tert-butyl-5-methyloxazole-4-carboxylic acid (40 mg, 98% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 2.61 (s, 3H), 1.38 (s, 9H) ppm.
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