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

HRID 339662

반응식

HRID 339662 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8b72e96bd29f41a38b067d733efbf1ca
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895550B2

연결된 노트

불러오는 중…