1,4-Dioxane → 7-(2-(Tert-butyldimethylsilyloxy)ethoxy)-6-fluoroquinoline-2-carbaldehyde

HRID 339062노트

반응식

HRID 339062 반응식
[Si:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([CH3:22])=[N:19]2)=[CH:14][C:13]=1[F:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[O:24]1CCOCC1>O>[Si:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([CH:22]=[O:24])=[N:19]2)=[CH:14][C:13]=1[F:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 312751,4-DioxaneHCID 709833797-(2-(Tert-butyldimethylsilyloxy)ethoxy)-6-fluoro-2-methylquinoline

생성물 1

HCID 867075467-(2-(Tert-butyldimethylsilyloxy)ethoxy)-6-fluoroquinoline-2-carbaldehyde수율 94%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of 7-(2-(tert-butyldimethylsilyloxy)ethoxy)-6-fluoro-2-methylquinoline (2.74 g, 8.17 mmol) in dioxane (24 mL) and water (0.24 mL) was added SeO2 (0.997 g, 8.98 mmol). The reaction mixture was heated at reflux for 4 hours. After cooling to ambient temperature, the solid was removed by filtration and washed with DCM. The filtrate was concentrated under reduced pressure and The residue was purified by flash chromatography on silica gel (4:1 hexanes/EtOAc) to give 7-(2-(tert-butyldimethylsilyloxy)ethoxy)-6-fluoroquinoline-2-carbaldehyde (2.69 g, 94%).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 hours
  3. customthe solid was removed by filtration
  4. washwashed with DCM
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (4:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-ac39514543f8479997cab4ae1c92463c
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

반응 노트

불러오는 중…