4-Methylindole → 4-Methylindoline

HRID 53151

反応式

HRID 53151 の反応式
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[BH3-]C#N.[Na+]>C(O)(=O)C>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][NH:6]2

参加物

4

反応物 2

HCID 852824-MethylindoleHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 5837034-Methylindoline収率 92.2%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of 4-methylindole (7.433 g, 0.0567 mol) in 100 mL of glacial acetic acid was added NaCNBH3 (7.25 g, 0.12 mol) portionwise over 1.5 h. The reaction mixture was then concentrated in vacuo water was added and the solution was basified with 10N NaOH. The resulting mixture was extracted with ethyl acetate (×3) and the organic extract was washed (brine), dried (Na2SO4) and evaporated to give an oil. Flash chromatography (SiO2 /ethyl acetate-hexane, 1:4) of this oil gave pure 4-methylindoline (6.962 g, 92%) as an oil: 1H NMR (DMSO-d6, 200 MHz) δ6.78 (t, J=7.6 Hz, 1H), 6.33 (d, J=7.4 Hz, 1H), 6.30 (d, J=7.6 Hz, 1H), 5.36 (br s, 1H), 3.38 (t, J=8.5 Hz, 2H), 2.81 (t, J=8.5 Hz, 2H), 2.11 (s, 3H).

後処理

  1. concentrationThe reaction mixture was then concentrated in vacuo water
  2. additionwas added
  3. extractionThe resulting mixture was extracted with ethyl acetate (×3)
  4. extractionthe organic extract
  5. washwas washed (brine)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customto give an oil

出典と根拠

ORDレコード
ord-018dd87bdd534d888b93dd1b102cb8bb
出典データセット
uspto-grants-1997_04
特許番号
US05618816

関連ノート

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