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

To a solution of methyl 6-methoxynicotinate (1.00 g, 5.98 mmol) in 20 mL of tetrahydrofuran at 0° C. under an atmosphere of nitrogen was added lithium aluminum hydride (1.0 M in tetrahydrofuran, 9.0 mL, 9.0 mmol) dropwise. After 30 min, the mixture was warmed to ambient temperature, and after 30 min, the mixture was cooled 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 with magnesium sulfate and warmed to ambient temperature. 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. temperaturethe mixture was cooled to 0° C.
3. dry with materialThe mixture was dried with magnesium sulfate
4. temperaturewarmed to ambient temperature
5. waitAfter 15 min
6. filtrationthe mixture was filtered through Celite
7. concentrationconcentrated in vacuo

ORD record

ord-062d5e73976149568e09e064716a2fb5

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697690B2