[1-(Propan-2-yl)-1H-indol-6-yl]methanol → 1-Isopropyl-1H-indole-6-carbaldehyde

HRID 1510131Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1510131
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:13][OH:14])[CH:11]=2)[CH:6]=[CH:5]1)([CH3:3])[CH3:2]>C(Cl)(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:13]=[O:14])[CH:11]=2)[CH:6]=[CH:5]1)([CH3:3])[CH3:2]

Komponenten

4

Edukt 1

HCID 29038143[1-(Propan-2-yl)-1H-indol-6-yl]methanol

Produkt 1

HCID 290381421-Isopropyl-1H-indole-6-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of (1-isopropyl-1H-indol-6-yl)methanol (0.18 g, 0.97 mmol) in CCl4(5 mL) was added manganese dioxide (0.13 g, 1.45 mmol). After stirring at 60° C. for 1 h, then 77° C. for 2 h, filtered reaction mixture through celite and concentrated. Partitioned crude compound between saturated sodium bicarbonate and EtOAc, washed with H2O and brine, dried with Na2SO4, and concentrated. The crude compound was chromatographed to give the desired product.

Aufarbeitung

  1. wait77° C. for 2 h
  2. filtrationfiltered
  3. customreaction mixture through celite and
  4. concentrationconcentrated
  5. customPartitioned crude compound between saturated sodium bicarbonate and EtOAc
  6. washwashed with H2O and brine
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated
  9. customThe crude compound was chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-e1c64bb396604cc2a93274fa62715ab7
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08211904B2

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