Bromide ion → 6-Methoxychromone

HRID 974787Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 974787
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]=[CH:6][C:5]2=[O:12].[CH3:13]OS(OC)(=O)=O.[Br-].C([O-])(O)=O.[Na+]>O.C(Cl)Cl>[CH3:13][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]=[CH:6][C:5]2=[O:12]

Komponenten

7

Edukt 4

HCID 259Bromide ionHCID 6497Dimethyl SulfateHCID 516892Sodium BicarbonateHCID 107970646-Hydroxy-4H-1-benzopyran-4-one

Produkt 1

HCID 6888806-MethoxychromoneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 6-hydroxychromone (4.5 g; 27.7 mmol), CH2Cl2 (150 ml), water (150 ml), dimethylsulphate (4 ml; 41.5 mmol), benzyltributylammmonium bromide (2 g; 5.5 mmol) and NaHCO3 (1.67 g; 41.5 mmol) was stirred for 24 hours at ambient temperature. The organic phase was decanted, washed with water, a dilute solution of ammonium hydroxide and with 1N HCl, it was dried over MgSO4 and evaporated. It was purified by chromatography, eluting with ethyl acetate/petroleum ether (50/50) to give 6-methoxychromone (4 g; 83%) as a brown solid.

Aufarbeitung

  1. customThe organic phase was decanted
  2. washwashed with water
  3. dry with materiala dilute solution of ammonium hydroxide and with 1N HCl, it was dried over MgSO4
  4. customevaporated
  5. customIt was purified by chromatography
  6. washeluting with ethyl acetate/petroleum ether (50/50)

Quellen und Nachweise

ORD-Eintrag
ord-0628306ae36d4ee0b995254fdb6584c1
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05607928

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