Hexane → Cyclopropyl(6-methoxypyridin-3-yl)methanol

Temperature

-78 °C

To a stirred −78° C. solution of 5-bromo-2-methoxypyridine (3.70 g, 19.79 mmol) in tetrahydrofuran (10 mL) was added 2.6 M n-butyllithium solution in hexane (8.4 mL, 21.84 mmol). The mixture was allowed to stir at −78° C. for 30 min, and then cyclopropanecarboxaldehye (1.70 g, 23.74 mmol) was added in one portion. The cooling bath was removed, and the mixture was allowed to warm to room temperature. After 2 h, the mixture was quenched by the addition of saturated aqueous ammonium chloride solution (100 mL). The resulting mixture was extracted with ethyl acetate (3×100 mL). The combined organic phases were dried over sodium sulfate, filtered, and concentrated. Chromatographic purification of the residue (silica gel, 20% ethyl acetate in petroleum ether elute) afforded 2.90 g (80%) of cyclopropyl(6-methoxypyridin-3-yl)methanol as a yellow oil.

1. customThe cooling bath was removed
2. temperatureto warm to room temperature
3. waitAfter 2 h
4. customthe mixture was quenched by the addition of saturated aqueous ammonium chloride solution (100 mL)
5. extractionThe resulting mixture was extracted with ethyl acetate (3×100 mL)
6. dry with materialThe combined organic phases were dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customChromatographic purification of the residue (silica gel, 20% ethyl acetate in petroleum ether elute)

ORD record

ord-d2b78490d67541138a8c9008f77e8c1a

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067914B1