Acetic Anhydride → 2-Pyridinemethanol, 2-acetate

Participants

Reaction Conditions

Reaction Steps

Compound 2,4-Dimethylpyridine N-Oxide (4.47 g, 36.3 mmol) was dissolved in Ac2O (11 mL) and added dropwise to acetic anhydride (108 mL) heated to 110° C. The resulting solution was stirred at 110° C. for 1 hour and 15 minutes. Excess reagent was evaporated leaving the corresponding 2-[(acetyloxy)-methyl]pyridine which was used without further purification. To a solution of the protected alcohol in MeOH (5 mL) was added NaOH 2N (15 mL) at room temperature. The mixture was stirred at room temperature for 1.5 hours, extracted with EtOAc and washed with water. The solvent was evaporated giving a residue that was purified by column chromatography (4% MeOH in CH2Cl2) affording 1.54 g (34% overall yield) of colorless oil. 1H NMR (CD3OD) δ 8.29 (d, 1H, J=4.2 Hz, H-6); 7.40 (s, 1H, H-3); 7.11 (d, 1H, J=4.2 Hz, H-5); 5.10 (s, 1H, OH); 4.68 (s, 2H, CH2); 2.38 (s, 3H); 13C NMR (CD3OD) δ 162.4 C-2), 151.0 (C-4), 149.4 (C-6), 125.0 (C-3), 123.3 (C-5), 65.8 (CH2), 21.7 (Me).

Provenance & Evidence