Potassium sodium tartarate → (2-Methoxypyridin-3-yl)methanol

Temperature

0 °C

A solution of 2-methoxy-nicotinic acid methyl ester (4.42 g, 26.5 mmol) in tetrahydrofuran (7 mL) was added via an addition funnel over a period of 15-20 min to a cooled (0° C.) mixture of lithium aluminum hydride (1.22 g, 32.1 mmol) in tetrahydrofuran (20 mL). The mixture was stirred at 0° C. for 40 min and then at room temperature for 3 h. The reaction mixture was poured into a solution of potassium sodium tartrate (10% w/v) and the resulting mixture was stirred at room temperature for 25 min. The mixture was filtered through a pad of Celite, washing with ethyl acetate (400 mL). The organic layer of the filtrate was separated and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine (100 mL), dried (magnesium sulfate), filtered and purified using a Biotage 40M system, eluting with 30% ethyl acetate/hexanes, to give (2-methoxy-pyridin-3-yl)-methanol (2.97 g, 81%) as a white solid.

1. temperaturea cooled
2. waitat room temperature for 3 h
3. stirringthe resulting mixture was stirred at room temperature for 25 min
4. filtrationThe mixture was filtered through a pad of Celite
5. washwashing with ethyl acetate (400 mL)
6. customThe organic layer of the filtrate was separated
7. extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
8. washThe combined organic layers were washed with brine (100 mL)
9. dry with materialdried (magnesium sulfate)
10. filtrationfiltered
11. custompurified
12. washeluting with 30% ethyl acetate/hexanes

ORD record

ord-5f9ad209f8234c9fab9cc99c6568def6

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622492B2