Methyl iodide → 2,3-Dihydro-4-hydroxy-7-methoxy-4-methyl-4H-1-benzopyran

HRID 236978Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 236978
[CH3:1]I.[Mg].[CH3:4][O:5][C:6]1[CH:16]=[CH:15][C:9]2[C:10](=[O:14])[CH2:11][CH2:12][O:13][C:8]=2[CH:7]=1.[Cl-].[NH4+]>CCOCC>[OH:14][C:10]1([CH3:1])[C:9]2[CH:15]=[CH:16][C:6]([O:5][CH3:4])=[CH:7][C:8]=2[O:13][CH2:12][CH2:11]1

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 43875107-methoxy-3,4-dihydro-2H-1-benzopyran-4-oneHCID 5462224Magnesium

Produkt 1

HCID 203045882,3-Dihydro-4-hydroxy-7-methoxy-4-methyl-4H-1-benzopyran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel3×

Versuchsvorschrift

Methyl iodide (145 g; 64.2 ml) in dry ether (50 ml) was added dropwise with stirring to magnesium turnings (22 g) in dry ether (730 ml). After the initial reaction had ceased the reaction mixture was refluxed for 1/2 hour, cooled and 2,3-dihydro-7-methoxy-4-oxo-4H-1-benzopyran, (77.9 g) in dry ether (440 ml) was added dropwise with stirring. After addition the reaction mixture was refluxed for 1 hour, cooled and the complex was decomposed by the addition of ammonium chloride solution. The ethereal layer was separated, washed with water and dried. Evaporation of the solvent left 76 g of the title compound as an oil (89%). MS and NMR analysis were correct for the required compound.

Aufarbeitung

  1. customAfter the initial reaction
  2. temperaturewas refluxed for 1/2 hour
  3. temperaturecooled
  4. additionAfter addition the reaction mixture
  5. temperaturewas refluxed for 1 hour
  6. temperaturecooled
  7. customThe ethereal layer was separated
  8. washwashed with water
  9. customdried
  10. customEvaporation of the solvent
  11. waitleft 76 g of the title compound as an oil (89%)

Quellen und Nachweise

ORD-Eintrag
ord-372e47da50834c18af7675729686de0d
Quelldatensatz
uspto-grants-1979_06
Patentnummer
US04159273

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