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Methyl iodide → 6-Methoxy-1,3,3-trimethylindolin-2-one

HRID 892202
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HRID 892202 반응식
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:14])([CH3:13])[C:8](=[O:12])[NH:9]2)=[CH:5][CH:4]=1.[H-].[Na+].I[CH3:18]>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:14])([CH3:13])[C:8](=[O:12])[N:9]2[CH3:18])=[CH:5][CH:4]=1
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참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 222416036-Methoxy-3,3-dimethylindolin-2-one

생성물 1

HCID 219318586-Methoxy-1,3,3-trimethylindolin-2-one

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a cooled solution (−5°−0° C.) of 6-methoxy-3,3-dimethyl-1,3-dihydro-indol-2-one (600 mg, 3.14 mmol, example 78) in THF (10.5 mL) is added 60% NaH (132 mg, 3.30 mmol) and is stirred for 15 min. Iodomethane (215 μL, 3.45 mmol) is added to the reaction mixture and stirred for 2 hrs. Quenched reaction with sat NH4Cl soln and diluted with EtOAc. Washed organic layer with sat NH4Cl soln, brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (silica, 30% ethyl acetate in hexanes) to give the title compound as a white crystalline solid. MS (ESI) 206 (M+H)+.

후처리

  1. stirringstirred for 2 hrs
  2. customQuenched
  3. customreaction with sat NH4Cl soln
  4. dry with materialWashed organic layer with sat NH4Cl soln, brine, dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography (silica, 30% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-9cb1dfb2d96f49acb1bb59a35cba22ac
출처 데이터셋
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07005440B1

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