Potassium Carbonate → 5-Bromo-3-methoxy-2-(2-trimethylsilanylethoxymethoxy)benzaldehyde

HRID 12293

Reaktionsgleichung

Reaktionsgleichung von HRID 12293
[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([O:10][CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2622385-Bromo-2-hydroxy-3-methoxybenzaldehydeHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Produkt 1

HCID 860709695-Bromo-3-methoxy-2-(2-trimethylsilanylethoxymethoxy)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

10 g of 5-bromo-2-hydroxy-3-methoxybenzaldehyde, 23.9 g of potassium carbonate and 12.2 g of (2-chloromethoxyethyl)trimethylsilane is suspended in 500 ml of DMF and stirred at room temperature for 48 hours. The DMF is distilled off in vacuo, the residue is dissolved in ethyl acetate, and the resulting solution is extracted with water. It is then dried over magnesium sulphate and filtered, and the solvent is distilled off. The crude product is purified by silica gel chromatography (heptane/ethyl acetate).

Aufarbeitung

  1. distillationThe DMF is distilled off in vacuo
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. extractionthe resulting solution is extracted with water
  4. dry with materialIt is then dried over magnesium sulphate
  5. filtrationfiltered
  6. distillationthe solvent is distilled off
  7. customThe crude product is purified by silica gel chromatography (heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-ec95a085efed4ea4bd8fe4a25e73c26c
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727989B2

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