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Methyl iodide → 7-Allyloxy-5-methoxy-2,2-dimethyl-4-oxochromane

HRID 494958
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 494958
[CH2:1]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:17])[CH2:10][C:11]([CH3:16])([CH3:15])[O:12]2)=[C:7]([OH:18])[CH:6]=1)[CH:2]=[CH2:3].[C:19](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:17])[CH2:10][C:11]([CH3:15])([CH3:16])[O:12]2)=[C:7]([O:18][CH3:19])[CH:6]=1)[CH:2]=[CH2:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 576828337-Allyloxy-5-hydroxy-2,2-dimethyl-4-oxochromane

Produkt 1

HCID 576828717-Allyloxy-5-methoxy-2,2-dimethyl-4-oxochromaneAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel
HCID 8857
Ethyl Acetate
Lösungsmittel

Versuchsvorschrift

2.90 g of 7-allyloxy-5-hydroxy-2,2-dimethyl-4-oxochromane was dissolved in 50 ml of N,N-dimethylformamide. Thereafter, 2.42 g of potassium carbonate and 2.32 g of iodomethane were added to the reaction solution, and the obtained mixture was then stirred at room temperature for 3 days. Thereafter, the reaction solution was diluted with ethyl acetate. The resultant product was washed with a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain 2.79 g of the subject compound.

Aufarbeitung

  1. washThe resultant product was washed with a saturated sodium chloride aqueous solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under a reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-80ae0aa5cdef48888a5237c1c7144cb8
Quelldatensatz
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07538123B2

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