Acetic Anhydride → 1-(2,3-Dihydro-6-methoxy-1H-indol-1-yl)ethanone

HRID 1014337ノート

反応式

HRID 1014337 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1.[BH3-]C#N.[Na+].[C:16](OC(=O)C)(=[O:18])[CH3:17]>C(O)(=O)C>[C:16]([N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=2)[CH2:7][CH2:8]1)(=[O:18])[CH3:17]

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 766596-Methoxy-1H-indoleHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 594419921-(2,3-Dihydro-6-methoxy-1H-indol-1-yl)ethanone

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

To a solution of 6-(methyloxy)-1H-indole (5.0 g, 34 mmols) in acetic acid (150 mL) was added NaBH3CN (5.12 g, 81.6 mmol) in several small portions. After stirring overnight at rt, the solvent was removed, the residue redissolved in ethyl acetate (300 mL), washed with saturated NaHCO3 (600 mL), filtered through a cotton plug and concentrated under reduced pressure to provide the crude indoline. ESIMS (M+H)+=150. The residue was then dissolved in glacial acetic acid (150 mL) and acetic anhydride (3.45 g, 33.86 mmol) was added. After stirring at rt for two hrs, the solvent was removed, residue resuspended in ethyl acetate (200 mL), washed with saturated NaHCO3 (600 mL). The aqueous layer was extracted with ethyl acetate (200 mL). The organic layers were combined, filtered through a cotton plug, and concentrated under reduced pressure to provide 1-acetyl-6-(methyloxy)-2,3-dihydro-1H-indole which was used without any further purification. ESIMS (M+H)+=192.

後処理

  1. customthe solvent was removed
  2. dissolutionthe residue redissolved in ethyl acetate (300 mL)
  3. washwashed with saturated NaHCO3 (600 mL)
  4. filtrationfiltered through a cotton plug
  5. concentrationconcentrated under reduced pressure
  6. customto provide the crude indoline
  7. stirringAfter stirring at rt for two hrs
  8. customthe solvent was removed
  9. washwashed with saturated NaHCO3 (600 mL)
  10. extractionThe aqueous layer was extracted with ethyl acetate (200 mL)
  11. filtrationfiltered through a cotton plug
  12. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-e66e4b9032c84c608f10f09633cf04f7
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

反応ノート

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