Sodium Chloride → 5-(3-Chloropropoxy)-3-isopropoxypyridine

Under a nitrogen atmosphere, a solution of 5-isopropoxypyridin-3-ol (1.04 g, 6.80 mmol) in DMF (10 mL) was slowly added over 10 min to a cold (0-5° C.), stirring slurry of sodium hydride (0.25 g of an 80% dispersion in mineral oil, 8.33 mmol) in DMF (15 mL). The mixture was allowed to warm to ambient temperature and further stirred for 1 h. To this slurry was added drop-wise over 5 min, 1-chloro-3-iodopropane (1.67 g, 8.16 mmol), and the resulting dark brown mixture was stirred at ambient temperature for 4 h. Cold water (25 mL) was carefully added, followed by saturated NaCl solution (25 mL). The resulting mixture was extracted with ether (4×50 mL). The combined ether extracts were dried (MgSO4), filtered, and concentrated by rotary evaporation producing a dark-brown oil (0.92 g, 59.0%).

1. additionTo this slurry was added drop-wise over 5 min
2. extractionThe resulting mixture was extracted with ether (4×50 mL)
3. dry with materialThe combined ether extracts were dried (MgSO4)
4. filtrationfiltered
5. concentrationconcentrated by rotary evaporation

ORD record

ord-3b5510858f1f44388a48e1147ef23495

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627648B1