Methyl iodide → 6-Methoxy-3,3-dimethylindolin-2-one

HRID 988255ノート

反応式

HRID 988255 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]([CH3:13])[C:8](=[O:12])[NH:9]2)=[CH:5][CH:4]=1.[CH3:14]N(CCN(C)C)C.[Li]CCCC.IC>C1COCC1>[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

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 222415386-Methoxy-3-methyl-1,3-dihydro-indol-2-oneHCID 178418339Butyllithium

生成物 1

HCID 222416036-Methoxy-3,3-dimethylindolin-2-one収率 82.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-25 °C

実験手順

To a cooled solution (−78° C.) of 6-methoxy-3-methyl-1,3-dihydro-indol-2-one (679 mg, 3.83 mmol) in THF (13 mL) is added TMEDA (1.16 mL, 7.66 mmol) followed by dropwise addition of 2.5M n-BuLi (3.06 mL, 7.66 mmol). The mixture is stirred for 15 min then warmed to −25° C. Add dropwise iodomethane (275 μL, 4.40 mmol) and let stir for 30 min. The reaction is quenched with sat NH4Cl soln, warmed to room temp and diluted with EtOAc. The organic layer is washed with sat NH4Cl soin, brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 35% ethyl acetate/hexanes) to give 601 mg of title compound as a white crystalline solid. MS (ESI) 192 (M+H)+.

後処理

  1. stirringlet stir for 30 min
  2. customThe reaction is quenched with sat NH4Cl soln
  3. temperaturewarmed to room temp
  4. additiondiluted with EtOAc
  5. washThe organic layer is washed with sat NH4Cl soin
  6. dry with materialbrine, dried over MgSO4
  7. concentrationconcentrated
  8. customThe residue is purified by flash chromatography (eluting with 35% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-7cc7a28e9b074eac875ab85a67cea185
出典データセット
uspto-grants-2003_10
特許番号
US06635655B1

反応ノート

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