Sodium Chloride → 5-(3-Chloropropoxy)-3-(phenylmethoxy)pyridine

Under a nitrogen atmosphere, a solution of 5-(phenylmethoxy)-pyridine-3-ol (1.52 g, 7.56 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 (0.238 g of an 80% dispersion in mineral oil, 7.94 mmol) in DMF (15 mL). The mixture was allowed to stir and warm to ambient temperature over 1 h. Next, 1-chloro-3-iodopropane (1.85 g, 9.07 mmol) was added drop-wise over 5 min. The resulting dark-brown mixture was stirred at ambient temperature for 4 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 an 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
7. customto give an oil

ORD record

ord-2f24f7d47e284563a8fe202d5507abd5

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06441006B2