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

To lithium aluminium hydride (0.68 g, 18 mmol) suspended in dry THF (10 ml) was added dropwise a solution of methyl 6-methoxynicotinate (1 g, 6 mmol) in dry THF (5 ml). The reaction mixture was stirred for 2 h at r.t. then cooled (ice-bath) and quenched with water (2 ml) followed by the further addition of 1 N NaOH (6 ml) and water (2 ml). The cold-bath was removed and the mixture stirred for 30 min at r.t., filtered and concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate (3×). The combined organic extracts were washed with water, brine, dried (MgSO4), filtered and concentrated under reduced pressure to give a crude oil which was purified over silica gel (ethyl acetate/n-heptane 1:1): colorless oil 0.45 g (51%);

1. temperaturethen cooled (ice-bath)
2. customquenched with water (2 ml)
3. additionfollowed by the further addition of 1 N NaOH (6 ml) and water (2 ml)
4. customThe cold-bath was removed
5. stirringthe mixture stirred for 30 min at r.t.
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. additionThe residue was diluted with water
9. extractionextracted with ethyl acetate (3×)
10. washThe combined organic extracts were washed with water, brine
11. dry with materialdried (MgSO4)
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure
14. customto give a crude oil which
15. customwas purified over silica gel (ethyl acetate/n-heptane 1:1)

ORD record

ord-d7c652ff3ffd4450bec666a767506163

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07501406B2