Imidazole → 3,4-Dimethoxy-5-triisopropylsilanyloxybenzaldehyde

HRID 1161508

Reaktionsgleichung

Reaktionsgleichung von HRID 1161508
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[CH:5]=[O:6].N1C=CN=C1.Cl[Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22].O>CN(C=O)C.C(OCC)(=O)C>[CH3:13][O:12][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([O:1][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[C:9]=1[O:10][CH3:11])[CH:5]=[O:6]

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 962WaterHCID 139400Triisopropylsilyl chlorideHCID 1415133,4-Dimethoxy-5-hydroxybenzaldehyde

Produkt 1

HCID 866179213,4-Dimethoxy-5-triisopropylsilanyloxybenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3.2 g of 3-hydroxy-4,5-dimethoxybenzaldehyde in 50 ml of DMF there were added 1.49 g of imidazole and 4.5 ml of chlorotriisopropylsilane. The mixture was stirred at room temperature for 21 hours and 30 minutes. Water was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with ice-cooled 1N hydrochloric acid, water, saturated aqueous sodium hydrogencarbonate, water and saturated brine in that order, and dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give 3,4-dimethoxy-5-triisopropylsilanyloxybenzaldehyde (6.08 g) as a light yellow oil.

Aufarbeitung

  1. washThe organic layer was washed with ice-
  2. temperaturecooled 1N hydrochloric acid, water, saturated aqueous sodium hydrogencarbonate, water and saturated brine in that order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe desiccating agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Quellen und Nachweise

ORD-Eintrag
ord-ce3e7d53c13e4a0590460b96addc9d58
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816522B2

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