Phosphorus oxychloride → 7-chlorofuro[2,3-c]pyridin-3(2H)-one O-methyl oxime
Reaktionsgleichung
[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[CH:8][N+:9]([O-])=[CH:10][CH:11]=2)[O:6][CH2:5]1.P(Cl)(Cl)([Cl:16])=O>C(Cl)Cl>[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[C:8]([Cl:16])[N:9]=[CH:10][CH:11]=2)[O:6][CH2:5]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
To a solution of 3-(methoxyimino)-2,3-dihydrofuro[2,3-c]pyridine 6-oxide (5.35 mmol) in 30 mL DCM were added 2.9 mL phosphoryl chloride at 0° C. The mixture was heated to 50° C. for 7 h, concentrated in vacuo, redissolved in DCM and quenched with solid NaHCO3 and then water. The aqueous layer was extracted with DCM (2×). The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by CC (KP-SIL™ from Biotage) using Hept/EtOAc (8/2) gives the desired product as beige solid;