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

HRID 1510131Notes

Reaction equation

HRID 1510131 reaction equation
[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]

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e1c64bb396604cc2a93274fa62715ab7
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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