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

HRID 339062ノート

反応式

HRID 339062 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-ac39514543f8479997cab4ae1c92463c
出典データセット
uspto-grants-2014_11
特許番号
US08889704B2

反応ノート

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