Dimethylformamide → Bicyclo[2.2.1]hept-2-yloxy-4-Methoxybenzaldehyde

HRID 2210490

Reaktionsgleichung

Reaktionsgleichung von HRID 2210490
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:5](O)[CH:4]=1.CN(C)[CH:14]=[O:15].C(=O)([O-])[O-].[K+].[K+].[CH2:23]1[CH:27]2C[CH:29](Br)[CH:25]([CH2:26]2)[CH2:24]1>O>[CH:27]12[CH2:26][CH:25]([CH2:24][CH2:23]1)[CH2:29][CH:14]2[O:15][C:4]1[CH:5]=[C:7]([O:8][CH3:9])[CH:10]=[CH:11][C:3]=1[CH:2]=[O:1]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12127IsovanillinHCID 982322-Norbornyl bromide

Produkt 1

HCID 18971811Bicyclo[2.2.1]hept-2-yloxy-4-Methoxybenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Isovanillin (50 g, 0.328 mol) is placed in a 1 liter round bottom flask which is equipped with a stir bar and reflux condensor and is charged with 500 ml of dimethylformamide. Potassium carbonate (45.3 g, 0.328 mol) is added to the reaction mixture which is heated to 80° C. At this temperature exo-2-bromonorbornane (12.57 g, 0.072 mol, 0.219 equivalents) is added and the reaction mixture is heated to 120° C. for 48 hours. The reaction is then cooled to room temperature and poured into 300 ml of water. The aqueous layer is extracted with ethyl ether (3×100 ml). The ethereal layer is washed with 1N sodium hydroxide solution (4×100 ml), water (3×100 ml) and saturated sodium chloride solution (3×100 ml). The organic layer is dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield 15.47 g of a green/brown oil. The crude product is purified by flash chromatography using a gradient eluent system of ethyl acetate/hexane [10% ethyl acetate/hexane→20% ethyl acetate/hexane] to yield 7.76 g (14.4%) of the aldehyde as a white solid. MP: 75.5° C.-79.5° C.

Aufarbeitung

  1. customwhich is equipped with a stir bar
  2. temperaturereflux condensor
  3. temperaturethe reaction mixture is heated to 120° C. for 48 hours
  4. temperatureThe reaction is then cooled to room temperature
  5. extractionThe aqueous layer is extracted with ethyl ether (3×100 ml)
  6. washThe ethereal layer is washed with 1N sodium hydroxide solution (4×100 ml), water (3×100 ml) and saturated sodium chloride solution (3×100 ml)
  7. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bd79c2394e17454c8bf522e23219cf5c
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05459145

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