6-Chloro-1,3-dihydroindol-2-one → Z-3-[4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butylidene]-6-chloro-1,3-dihydro-indol-2-one

HRID 2065409ノート

反応式

HRID 2065409 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[C:12]([Si:16]([CH3:26])([CH3:25])[O:17][CH2:18][C:19]([CH3:24])([CH3:23])[CH2:20][CH:21]=O)([CH3:15])([CH3:14])[CH3:13].C[O-].[Na+]>CO>[C:12]([Si:16]([CH3:25])([CH3:26])[O:17][CH2:18][C:19]([CH3:24])([CH3:23])[CH2:20]/[CH:21]=[C:6]1\[C:7](=[O:11])[NH:8][C:9]2[C:5]\1=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)([CH3:15])([CH3:14])[CH3:13]

参加物

5

反応物 3

HCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 104896714-(Tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butyraldehydeHCID 10942334Sodium Methoxide

生成物 1

HCID 86656668Z-3-[4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butylidene]-6-chloro-1,3-dihydro-indol-2-one収率 85.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To the mixture of 6-chlorooxindole (2.1 g, 12.6 mmol) (Crescent) and 4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butyraldehyde (2.9 g, 12.6 mmol) in methanol (80 mL) was added a methanolic solution (25%, Aldrich) of sodium methoxide (4.08 g, 18.9 mmol) dropwise. The reaction mixture was stirred at room temperature for 10 min. The solvent was removed, and the residue was partitioned between ethyl acetate and water. The organic layer was separated, dried over Na2SO4, and concentrated. The residue was purified by chromatography (20% EtOAc in hexanes) to give E/Z-3-[4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butylidene]-6-chloro-1,3-dihydro-indol-2-one as a yellow oil (Yield 4.1 g, 84%).

後処理

  1. customThe solvent was removed
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (20% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-9a1a800f81fe439da393717fe4096749
出典データセット
uspto-grants-2012_10
特許番号
US08288431B2

反応ノート

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