Toluene → (1H-indol-5-yl)methanol

HRID 456906

반응식

HRID 456906 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10](O)=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1(C)C=CC=CC=1>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][OH:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

참가 물질

5

반응물 3

HCID 1140TolueneHCID 742801H-Indole-5-Carboxylic AcidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 2773458(1H-indol-5-yl)methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mechanically stirred solution of 1H-Indole-5-carboxylic acid (5-1, 20.01 g, 124 mmol) in THF (500 mL) was added at ambient temperature slowly a solution of 1M-LAH in toluene (186 mL, 186 mmol, 1.5 equiv). The reaction mixture was heated at reflux for 1 hour, quenched with ice, partitioned between ethylacetate and saturated aqueous NaHCO3. The organic layer was washed with brine, separated, dried (MgSO4) and concentrated in vacuo. The crude product solidified upon standing under the reduced pressure. The crude solid was suspended in hexanes (200 mL) and ethyl acetate (10 mL), stirred overnight, collected by filtration and air-dried to afford the desired product as a light brown solid. 1H NMR (400 MHz, CDCl3) δ 8.24 (br s, 1H), 7.62 (s, 1H), 7.36 (d, 1H, J=8.4 Hz), 7.23 (d, 1H, J=8.4 Hz), 7.20 (s, 1H), 6.54 (s, 1H), 4.75 (s, 2H), 1.68 (s, 1H).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 hour
  3. customquenched with ice
  4. custompartitioned between ethylacetate and saturated aqueous NaHCO3
  5. washThe organic layer was washed with brine
  6. customseparated
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. filtrationcollected by filtration
  10. customair-dried

출처 및 근거

ORD 기록
ord-6c943432ae3740ab89f261a94a6bebea
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186723B2

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