Water → (6-Methoxypyridin-3-yl)methanol

To a solution of methyl 6-methoxynicotinate (1.00 g, 5.98 mmol) in 20 mL of THF at 0° C. under an atmosphere of nitrogen was added lithium aluminum hydride (1.0 M in THF, 9.0 mL, 9.0 mmol) dropwise. After 30 min, the reaction was warmed to rt, and after 30 min, the reaction was recooled to 0° C., diluted with diethyl ether, and treated with water (0.34 mL), 15% aqueous sodium hydroxide (0.34 mL), and additional water (1.02 mL). The mixture was dried over magnesium sulfate and warmed to rt. After 15 min, the mixture was filtered through celite and concentrated in vacuo to provide (6-methoxypyridin-3-yl)methanol that gave a proton NMR spectra consistent with theory.

1. waitafter 30 min
2. customwas recooled to 0° C.
3. dry with materialThe mixture was dried over magnesium sulfate
4. temperaturewarmed to rt
5. waitAfter 15 min
6. filtrationthe mixture was filtered through celite and
7. concentrationconcentrated in vacuo

ORD record

ord-edd03c1765a0428fae7e6966039da7f7

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815902B2