Acetaldehyde, 2,2-dimethoxy- → 3-(4,7-Dihydroxy-5-methyl-2-oxo-2H-chromene-3-yl)-7-hydroxy-9-methyl-2-methoxy-2,3-dihydro-4H-furo[3.2-c]chromene-4-one

HRID 131660

Reaktionsgleichung

Reaktionsgleichung von HRID 131660
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:13])=[CH:9][C:10]=2[CH3:12])[O:5][C:4](=[O:14])[CH:3]=1.[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH:18]=O>CO>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:13])=[CH:9][C:10]=2[CH3:12])[O:5][C:4](=[O:14])[C:3]=1[CH:18]1[C:3]2[C:4](=[O:14])[O:5][C:6]3[CH:7]=[C:8]([OH:13])[CH:9]=[C:10]([CH3:12])[C:11]=3[C:21]=2[O:20][CH:17]1[O:16][CH3:15]

Komponenten

4

Edukt 2

HCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 547077754,7-Dihydroxy-5-methylcoumarin

Produkt 1

HCID 867606893-(4,7-Dihydroxy-5-methyl-2-oxo-2H-chromene-3-yl)-7-hydroxy-9-methyl-2-methoxy-2,3-dihydro-4H-furo[3.2-c]chromene-4-oneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

4,7-Dihydroxy-5-methylcoumarin (200 mg; 1.04 mmole) was dissolved in methanol (5 mL). A 60% aqueous dimethoxyacetaldehyde solution (792 μL; 8.7 mmole) was added and the reaction mixture was refluxed for 5 hours. By cooling to room temperature a white precipitate was precipitated, which was filtered off and washed with methanol. Obtained was the title compound in a 92% yield and of sufficient purity to be used in the next synthesis step:

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed for 5 hours
  2. customwas precipitated
  3. filtrationwhich was filtered off
  4. washwashed with methanol
  5. customObtained

Quellen und Nachweise

ORD-Eintrag
ord-95b24f291c7d40b5b049ff1f6c9402c9
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384975B2

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