Phosphorus oxychloride → 4-(Benzyloxy)-2-chloropyridine

4-Benzyloxy-2-pyridone (26.3 g, 0.131 mol) and POCl3 (200 mL) was heated at reflux for 2 h. The mixture was cooled and poured into 1 L of crushed ice and then 500 mL of ethyl acetate was added. The mixture was treated with decolorizing carbon, filtered and then treated with solid potassium carbonate until gas ceased to evolve. The mixture was filtered and the layers were separated. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were treated with decolorizing carbon, dried (MgSO4), filtered and the solvent was removed in-vacuo. The crude product was chromatographed to give 2-chloro-4-benzyloxypyridine (8 g, 28% yield) as a white solid, mp=91° C. -93° C. Anal. Calcd. for C12H10NO: C,65.61; H,4.59; N,6.38 Found: C,,65.59; H,4.55; N,6.39.

1. temperatureat reflux for 2 h
2. temperatureThe mixture was cooled
3. additionThe mixture was treated with decolorizing carbon
4. filtrationfiltered
5. additiontreated with solid potassium carbonate until gas
6. filtrationThe mixture was filtered
7. customthe layers were separated
8. extractionThe aqueous layer was extracted three times with ethyl acetate
9. additionThe combined organic layers were treated with decolorizing carbon
10. dry with materialdried (MgSO4)
11. filtrationfiltered
12. customthe solvent was removed in-vacuo
13. customThe crude product was chromatographed

ORD record

ord-3a4dbc64018946f7914b70f2f18d7540

Source dataset

uspto-grants-1996_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05484761