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

HRID 892201ノート

反応式

HRID 892201 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

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, example 77) 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 15 min then warmed to −25° C. Iodomethane (275 μL, 4.40 mmol) is added dropwise and stirred for 30 min. Reaction is quenched with sat NH4Cl soln, warmed to room temp 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, 35% ethyl acetate in hexanes) to give the title compound as a white crystalline solid. MS (ESI) 192 (M+H)+.

後処理

  1. stirringstirred for 30 min
  2. customReaction
  3. customis quenched with sat NH4Cl soln
  4. temperaturewarmed to room temp
  5. additiondiluted with EtOAc
  6. dry with materialWashed organic layer with sat NH4Cl soln, brine, dried over MgSO4
  7. concentrationconcentrated
  8. customThe residue is purified by flash chromatography (silica, 35% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-d257a4a7c4b94205a56784f4e7b3df6e
出典データセット
uspto-grants-2006_02
特許番号
US07005440B1

反応ノート

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