Sodium borohydride → (2-Methoxypyridin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of NaBH4 (0.075 g, 2.04 mmol) in absolute EtOH (10 mL) was dropwise added a solution of 2-methoxy-pyridine-3-carbaldehyde (0.98 g, 7.15 mmol) in EtOH (2 mL) at −40° C. under N2. The reaction mixture was stirred at −40° C. for 45 min and then carefully quenched with brine. After warmed up to room temperature, the reaction solvent was removed and then diluted with EtOAc and water. The aqueous layer was extracted with EtOAc (×2) and the combined organics were washed with water, brine and dried over anhydrous Na2SO4. The mixture was filtered through Celite-silica gel. The concentration under the reduced pressure provided the product, which was carried to the next step without further purification. 1H NMR (300 MHz, CDCl3) 8.13 (m, 1H), 7.63 (m, 1H), 6.90 (m, 1H), 4.67 (s, 2H), 4.02 (s, 3H).

Provenance & Evidence