Sodium Hydroxide → 2-Chlorofuro[3,2-b]pyridine

Reaktionsgleichung

[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:4]=2[CH2:3][C:2]1=O.[OH-].[Na+].P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:4]=2[CH:3]=1

Komponenten

Edukt 3

HCID 14798Sodium Hydroxide

HCID 24813Phosphorus oxychloride

HCID 13384344Furo[3,2-B]pyridin-2(3H)-one

Produkt 1

HCID 107255602-Chlorofuro[3,2-b]pyridine

Versuchsvorschrift

Furopyridone (6, 3.26 g, 24.15 mmol) is treated with phosphorus oxychloride (10 ml) at refluxing temperature for 3 hours. After cooling, the dark solution is poured into ice and basified with aqueous sodium hydroxide to pH ˜9. The mixture is extracted with chloroform. After evaporation of the chloroform, the brown oil is applied to flash column chromatography on silica gel to give chlorofuropyridine as yellow crystalline solid (7).