Sodium Chloride → 4-Chloro-1-(3-pyridyloxy)butane

Under a nitrogen atmosphere, a solution of 3-hydroxypyridine (3.50 g, 36.8 mmol) in N,N-dimethylformamide (DMF) (10 mL) was added drop-wise over 5 min to a cold (0-5° C.), stirring slurry of sodium hydride (1.16 g of an 80% dispersion in mineral oil, 38.6 mmol) in DMF (40 mL). The mixture was allowed to stir and warm to ambient temperature over 1 h. The mixture was then cooled to 0-5° C., and 1-chloro-4-iodobutane (9.67 g, 44.2 mmol) was added drop-wise over 5 min. The resulting dark-brown mixture was stirred at ambient temperature for 2 h. Water (25 mL) was added, followed by saturated NaCl solution (25 mL), and the mixture was extracted with ether (4×50 mL). The combined ether extracts were dried (Na2SO4), filtered, and concentrated by rotary evaporation to a residue that was dried briefly under high vacuum to give 6.89 g (quantitative yield) of an oil.

1. temperatureThe mixture was then cooled to 0-5° C.
2. stirringThe resulting dark-brown mixture was stirred at ambient temperature for 2 h
3. extractionthe mixture was extracted with ether (4×50 mL)
4. dry with materialThe combined ether extracts were dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated by rotary evaporation to a residue that
7. customwas dried briefly under high vacuum

ORD record

ord-950ae041233f4c1a828ebae754829700

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627648B1