4-Methylindole → 4-Methylindoline

HRID 53151

반응식

HRID 53151 반응식
[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

참가 물질

4

반응물 2

HCID 852824-MethylindoleHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 5837034-Methylindoline수율 92.2%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-018dd87bdd534d888b93dd1b102cb8bb
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618816

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