Imidazole → 8-(Tert-butyldimethylsilyloxy)quinoline-2-carbaldehyde

HRID 876383

Reaktionsgleichung

Reaktionsgleichung von HRID 876383
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]=[O:13])[CH:8]=[CH:7]2.N1C=CN=C1.[C:19]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])([CH3:21])[CH3:20]>C(Cl)Cl>[Si:23]([O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]=[O:13])[CH:8]=[CH:7]2)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:25])[CH3:24]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 5993428-Hydroxy-2-quinolinecarboxaldehyde

Produkt 1

HCID 585670828-(Tert-butyldimethylsilyloxy)quinoline-2-carbaldehydeAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 8-hydroxyquinoline-2-carbaldehyde (15.0 g, 86.62 mmol) and imidazole (12.97 g, 190.6 mmol) in anhydrous CH2Cl2 (250 mL) at 0° C. was added tert-butylchlorodimethylsilane (14.36 g, 95.28 mmol). The mixture was allowed to warm slowly to ambient temperature over 16 hours and then partitioned between CH2Cl2 and water. The aqueous phase was extracted with CH2Cl2 and the combined organic phases were washed successively with saturated NaHCO3, water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel pad filtration eluting with hexanes followed by 19:1 ethyl acetate/hexanes to provide 23.69 g (95%) of desired product as a dark yellow oil.

Aufarbeitung

  1. custompartitioned between CH2Cl2 and water
  2. extractionThe aqueous phase was extracted with CH2Cl2
  3. washthe combined organic phases were washed successively with saturated NaHCO3, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. filtrationThe residue was purified by silica gel pad filtration
  8. washeluting with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-dce37435330049cb8a94a5fc1ae3ea15
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987251B2

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