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

HRID 339662

Reaction equation

HRID 339662 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 585670828-(Tert-butyldimethylsilyloxy)quinoline-2-carbaldehydeYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-Hydroxyquinoline-2-carbaldehyde (5.00 g, 28.9 mmol) and imidazole (4.32 g, 63.5 mmol) were dissolved in DCM (50 mL) under N2. The reaction mixture was cooled to 0° C. after which time tert-butylchlorodimethylsilane (4.94 g, 31.8 mmol) was added. After stirring for 16 hours at ambient temperature, the reaction mixture was partitioned between DCM and H2O. The organic layer was washed with H2O and aqueous saturated NaHCO3, dried over Na2SO4, filtered and concentrated under reduced pressure to afford an orange oil. The residue was purified via flash column chromatography (10:1 Hexane/EtOAc) to provide 6.85 g (83%) of desired product as a yellow/orange oil.

Workup

  1. additionwas added
  2. customthe reaction mixture was partitioned between DCM and H2O
  3. washThe organic layer was washed with H2O and aqueous saturated NaHCO3
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford an orange oil
  8. customThe residue was purified via flash column chromatography (10:1 Hexane/EtOAc)

Sources & evidence

ORD record
ord-8b72e96bd29f41a38b067d733efbf1ca
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Linked notes

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