Chlorotrimethylsilane → 1-(1-Methyl-1H-indol-3-yl)-3-(4-pyridyl)-3-trimethylsilyloxypropan-1-one

HRID 362792ノート

反応式

HRID 362792 の反応式
C([Li])CCC.C(NC(C)C)(C)C.[C:13]([C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([CH3:25])[CH:17]=1)(=[O:15])[CH3:14].[N:26]1[CH:31]=[CH:30][C:29]([CH:32]=[O:33])=[CH:28][CH:27]=1.Cl[Si:35]([CH3:38])([CH3:37])[CH3:36]>C1COCC1>[CH3:25][N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]([C:13](=[O:15])[CH2:14][CH:32]([C:29]2[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=2)[O:33][Si:35]([CH3:38])([CH3:37])[CH3:36])=[CH:17]1

参加物

7

反応物 5

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 133894-PyridinecarboxaldehydeHCID 5941561-(1-Methyl-1H-indol-3-yl)ethanoneHCID 178418339Butyllithium

生成物 1

HCID 232995901-(1-Methyl-1H-indol-3-yl)-3-(4-pyridyl)-3-trimethylsilyloxypropan-1-one収率 51%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

1.6M n-Butyllithium (1.19 ml, 1.90 mmol) was added to dry THF (10 ml) containing diisopropylamine (0.266 ml, 1.90 mmol) under Ar at 0° C. After 15 mins, the mixture was cooled to -78° C., and 3-acetyl-1-methyl-1H-indole (0.300 g, 1.73 mmol) in dry THF (5 ml) was added slowly. The resulting mixture was left at -78° C. for 1 h, before pyridine-4-carboxaldehyde (0.165 ml, 1.73 mmol) was added. The reaction mixture was then left at -78° C. for 1 h, before being allowed to warm to 0° C., whereupon chlorotrimethylsilane (0.439 ml, 3.46 mmol) was added. The mixture was then allowed to warm to room temp and stirred for 1 h, before being evaporated under reduced pressure and partitioned between dichloromethane and water. The organic layer was then dried (Na2SO4) and evaporated under reduced pressure to give a pale yellow solid which was purified by silica-gel chromatography (EtOAc as eluant) to give the title compound as a yellow solid (0.300 g, 51%).

後処理

  1. additionwas added
  2. waitThe reaction mixture was then left at -78° C. for 1 h
  3. additionwas added
  4. temperatureto warm to room temp
  5. custombefore being evaporated under reduced pressure
  6. custompartitioned between dichloromethane and water
  7. dry with materialThe organic layer was then dried (Na2SO4)
  8. customevaporated under reduced pressure
  9. customto give a pale yellow solid which
  10. customwas purified by silica-gel chromatography (EtOAc as eluant)

出典と根拠

ORDレコード
ord-9b76f0a879d646e1a4ec574363aec2e4
出典データセット
uspto-grants-1999_02
特許番号
US05872134

反応ノート

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