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

Temperature

-40 °C

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).

1. customcarefully quenched with brine
2. temperatureAfter warmed up to room temperature
3. customthe reaction solvent was removed
4. additiondiluted with EtOAc and water
5. extractionThe aqueous layer was extracted with EtOAc (×2)
6. washthe combined organics were washed with water, brine
7. dry with materialdried over anhydrous Na2SO4
8. filtrationThe mixture was filtered through Celite-silica gel
9. concentrationThe concentration under the reduced pressure
10. customprovided the product, which
11. customwas carried to the next step without further purification

ORD record

ord-52c1b15abb5149be8a3abe13455e0cf8

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07803793B2