Toluene → (1H-indol-5-yl)methanol

HRID 456906

Reaktionsgleichung

Reaktionsgleichung von HRID 456906
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6c943432ae3740ab89f261a94a6bebea
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186723B2

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