General procedure for the synthesis of (2-methoxy-3-pyridine)methanol from methyl 2-methoxynicotinate:
Example 138: Preparation of (2-methoxy-3-pyridine)methanol
Methyl 2-methoxy-3-pyridinecarboxylate (1.021 g, 6.11 mmol) was dissolved in anhydrous tetrahydrofuran (5 mL) and lithium borohydride (0.266 g, 1.22 mmol) was added batchwise. The reaction mixture was heated to 70 °C and kept for 2 hours. Upon completion of the reaction, the reaction was quenched by the addition of saturated aqueous ammonium chloride, followed by three extractions with ethyl acetate (3×). The organic phases were combined, dried with magnesium sulfate and concentrated under reduced pressure to give (2-methoxy-3-pyridine)methanol as a colorless oil (0.849 g, 100% yield).
1H-NMR (400 MHz, CDCl3): δ 2.29 (1H, m, OH), 4.0 (3H, s, OCH3), 4.67 (2H, m, CH2), 6.89 (1H, m, Ar-H), 7.59 (1H, m, Ar-H), 8.1 (1H, m, Ar-H) ppm.
