Water → 3-(3-Chloro-propoxy)-pyridine

Under a nitrogen atmosphere, a solution of 3-hydroxypyridine (35.00 g, 0.368 mmol) in N,N-dimethylformamide (DMF) (150 mL) was slowly added drop-wise over 15 min to a cold (0-5° C.), stirring slurry of sodium hydride (17.64 g of an 80% dispersion in mineral oil, 0.588 mol) in DMF (250 mL). The mixture was allowed to stir and warm to ambient temperature over 1 h. The gray slurry was cooled to 0-5° C., and 1-chloro-3-iodopropane (90.3 g, 0.442 mol) was added drop-wise over 30 min. The resulting dark-brown mixture was allowed to stir and warm to ambient temperature over 16 h. Water (500 mL) was added and the mixture was divided into equal parts. Each half was diluted with saturated NaCl solution (200 mL) and extracted with ether (5×200 mL). All ether extracts were combined and concentrated to give 55.1 g (87.3%) of a dark-brown oil.

1. customover 15 min
2. customto a cold (0-5° C.)
3. temperatureThe gray slurry was cooled to 0-5° C.
4. stirringto stir
5. temperaturewarm to ambient temperature over 16 h
6. extractionextracted with ether (5×200 mL)
7. concentrationconcentrated

ORDレコード

ord-277ed51739ea411f9d4ca86f68821a5d

出典データセット

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06627648B1