6,3'-Dimethoxyflavone synthesis
- Product Name:6,3'-Dimethoxyflavone
- CAS Number:79786-40-6
- Molecular formula:C17H14O4
- Molecular Weight:282.29
Yield:79786-40-6 51%
Reaction Conditions:
with tetrahydropyrrole;iodine in dimethyl sulfoxide at 150; for 6 h;
Steps:
2-phenyl-4H-chromen-4-one (2).
General procedure: In a 100mL round bottom flask 1-(2-hydroxyphenyl)ethan-1-one (123μL, 1.00mmol, 1.0 equiv.) and benzaldehyde (101μL, 1.00mmol, 1.0 equiv.) were dissolved in DMSO (0.1M). Under stirring pyrrolidine (41μL, 500μmol, 50mol%) and iodine (13mg, 50μmol, 5mol%) were added and the mixture was heated to 150°C for 21h. After cooling to room temperature, the mixture was diluted with brine and extracted with ethyl acetate (3×5mL). The combined organic phases were washed with a saturated sodium thiosulfate solution and brine, then dried over sodium sulfate. It was filtered off and the solvent was evaporated under reduced pressure. The residue was purified over flash column chromatography (silica, cyclohexane/ethyl acetate 9:1→7:3). After trituration in diethylether (2×3mL) and removal of the solvent, the product was isolated as a brown solid (93mg, 418μmol, 42%).
References:
Kampschulte, Nadja;Berking, Tim;?elik, Ibrahim E.;Kirsch, Stefan F.;Schebb, Nils Helge [European Journal of Medicinal Chemistry,2022,vol. 238,art. no. 114332]
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