Vanillin → HCID 6484658, Verbindung

HRID 1012209Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1012209
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[CH3:12][O:13][CH2:14][CH2:15]Br.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O>[CH3:7][O:6][C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][C:8]=1[O:9][CH2:15][CH2:14][O:13][CH3:12])[CH:2]=[O:1]

Komponenten

6

Edukt 4

HCID 1183VanillinHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl ether

Produkt 1

HCID 6484658HCID 6484658, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a flask was added vanillin (3.28 g, 21.6 mmol) and 2-bromoethyl methyl ether (3.04 mL, 1.5 equiv) in a solution of DMF (20 mL). K2CO3 (5.5 g, 2 equiv) was then added to the solution and the reaction slurry was stirred at 90° C. for 16 h under N2. The reaction solution was diluted with EtOAc (100 mL), filtered, washed with sat NH4Cl, dried over Na2SO4, filtered and concentrated in vacuo. The crude material was chromatographed (SiO2, Hex/EtOAc 100:D to 70:30) to afford the intermediate compound.

Aufarbeitung

  1. filtrationfiltered
  2. washwashed with sat NH4Cl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was chromatographed (SiO2, Hex/EtOAc 100:D to 70:30)
  7. customto afford the intermediate compound

Quellen und Nachweise

ORD-Eintrag
ord-4c340c6134f34f71952ce12dda49b484
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977489B2

Notizen zur Reaktion

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