Formaldehyde → 2-(6-Methoxypyridin-2-yl)ethan-1-ol

Temperatur

-78 °C

1.6M n-Butyllithium/hexane solution (282 mL, 451.96 mmol) was added dropwise to a solution of 2-methoxy-6-methylpyridine (50.60 g, 410.87 mmol) in THF (625 mL) over 1 hr at −78° C. under argon atmosphere. The reaction mixture was stirred at −78° C. for 45 min, paraformaldehyde (49.3 g, 1643.49 mmol) was added thereto at −78° C., and the mixture was stirred vigorously at room temperature for 3.5 hr. The reaction mixture was poured into ice water (1000 mL), and NaCl was added thereto to give a saturated solution. The saturated solution was extracted with a mixed solvent of ethyl acetate/THF (3:1) (×3). The organic layer was washed with water and brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 8→50% ethyl acetate/hexane) to give 2-(6-methoxypyridin-2-yl)ethanol (23.22 g, 152 mmol, 37%) as a colorless oil.

1. stirringat −78° C., and the mixture was stirred vigorously at room temperature for 3.5 hr
2. additionwas added
3. customto give a saturated solution
4. extractionThe saturated solution was extracted with a mixed solvent of ethyl acetate/THF (3:1) (×3)
5. washThe organic layer was washed with water and brine
6. dry with materialdried over magnesium sulfate
7. customthe solvent was evaporated under reduced pressure
8. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 8→50% ethyl acetate/hexane)

ORD-Eintrag

ord-4f377e6bfab64d51a68200e2dbd8c104

Quelldatensatz

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09365520B2