Stannous Chloride → 7-Amino-3-iodo-8-methoxy-2-phenyl-chromen-4-one
Reaktionsgleichung
[I:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[C:6]([O:16][CH3:17])[C:7]([N+:13]([O-])=O)=[CH:8][CH:9]=2)[O:4][C:3]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl[Sn]Cl>C(OCC)(=O)C>[NH2:13][C:7]1[C:6]([O:16][CH3:17])=[C:5]2[C:10]([C:11](=[O:12])[C:2]([I:1])=[C:3]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:4]2)=[CH:9][CH:8]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a suspension of 3-iodo-8-methoxy-7-nitro-2-phenyl-chromen-4-one (903 mg, 2.1 mmol) in ethyl acetate (7 mL) and IMS (7 mL) was added SnCl2 (2.37 g, 10.5 mmol). The reaction mixture was stirred at 80° C. for 1.5 hours before cooling to cool to RT. The resultant mixture was partitioned between ethyl acetate and water and the phases separated. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were washed with brine, dried (NaSO4), filtered, and the solvent removed in vacuo. The resulting residue was subjected to flash chromatography (SiO2, gradient 40-50% ethyl acetate in cyclohexane) to give the title compound as a yellow solid (752 mg, 91%). LCMS (Method G): RT=3.35 min, [M+H]+=394.
Aufarbeitung
- temperaturebefore cooling
- temperatureto cool to RT
- customThe resultant mixture was partitioned between ethyl acetate and water
- customthe phases separated
- extractionThe aqueous layer was extracted with ethyl acetate
- washthe combined organic extracts were washed with brine
- dry with materialdried (NaSO4)
- filtrationfiltered
- customthe solvent removed in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-6deb19dd29004bb4bf3de08ea5d9c326
- Quelldatensatz
- uspto-grants-2013_10
- Patentnummer
- US08546376B2
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