Sodium Chloride → 3-(2-Chloroethoxy)pyridine

Under a nitrogen atmosphere, a solution of 3-hydroxypyridine (2.00 g, 21.0 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 (0.756 g of an 80% dispersion in mineral oil, 27.5 mmol) in DMF (15 mL). The mixture was allowed to stir and warm to ambient temperature over 1 h. Next, 1-bromo-2-chloroethane (3.60 g, 25.2 mmol) was added drop-wise over 5 min. The resulting dark-brown mixture was stirred at ambient temperature for 4 h. Water (30 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 3.96 g (66.1%) of a light-brown oil.

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

ORD record

ord-a75b5798eabd46e3a6e06e848d6789c6

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627648B1