Methyl 6-methoxypyridine-3-carboxylate → (6-Methoxypyridin-3-yl)methanol

Temperature

0 °C

A solution of methyl 6-methoxynicotinate (3.00 g, 17.9 mmol) in tetrahydrofuran (10 mL) was added via an addition funnel over a period of 10 min to a cooled (0° C.) mixture of lithium aluminum hydride (817 mg, 21.5 mmol) in tetrahydrofuran (18 mL). The mixture was stirred at 0° C. for 30 min and then at room temperature for 2 h. The reaction mixture was poured into a solution of potassium sodium tartrate (10% w/v; 100 mL) and the resulting mixture was stirred at room temperature for 20 min. The mixture was filtered through a pad of Celite, washing with ethyl acetate. 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 dried (magnesium sulfate), filtered and eluted through a silica plug using 40% ethyl acetate/hexanes to give (6-methoxy-pyridin-3-yl)-methanol (1.8 g, 72%) as a clear oil.

1. temperaturea cooled
2. waitat room temperature for 2 h
3. stirringthe resulting mixture was stirred at room temperature for 20 min
4. filtrationThe mixture was filtered through a pad of Celite
5. washwashing with ethyl acetate
6. customThe organic layer of the filtrate was separated
7. extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
8. dry with materialThe combined organic layers were dried (magnesium sulfate)
9. filtrationfiltered
10. washeluted through a silica plug

ORD record

ord-3ce4cc423e264f0fac714b5434b4e5ba

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622492B2