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 2065409노트

반응식

HRID 2065409 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-9a1a800f81fe439da393717fe4096749
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288431B2

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