[Synthesis]
General procedure for the synthesis of (5-methylisoxazol-3-yl)methanol from methyl 5-methylisoxazole-3-carboxylate: Methyl 5-methylisoxazole-3-carboxylate (14.12 g, 100 mmol) was dissolved in anhydrous THF (150 mL) and cooled to -75 °C in a dry ice/isopropanol bath to form a white suspension. A THF solution of 1 M lithium aluminum hydride (105 mL, 105 mmol) was slowly added, and the rate of addition was controlled to maintain the internal temperature below -55 °C. The reaction mixture gradually turned yellow and was subsequently allowed to warm slowly to room temperature and stirred overnight. The reaction mixture was again cooled to -75 °C, cold water was carefully added until gas release ceased, and then the pH was adjusted to 1-2 with aqueous 6N HCl. The reaction mixture became viscous and was concentrated under reduced pressure to remove the solvent. The residue was dissolved in toluene and azeotropized to remove water. After drying, the residue was washed with chloroform (3 x 100 mL), the chloroform solution was filtered to remove insoluble solids, and finally the solvent was evaporated to give the light yellow oily product (5-methylisoxazol-3-yl)methanol in a yield of 8.34 g (74% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 6.02 (s, 1H), 4.66 (s, 2H), 2.80-3.10 (m, 1H), 2.39 (s, 3H). |