HCID 19787126, compound → HCID 13050347, compound

HRID 1646758Notes

Reaction equation

HRID 1646758 reaction equation
[CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[CH2:13][OH:14])([CH3:3])[CH3:2]>C(OCC)(=O)C.[O-2].[O-2].[Mn+4]>[CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[CH:13]=[O:14])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 19787126HCID 19787126, compound

Product 1

HCID 13050347HCID 13050347, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 3-isopropyl-2-hydroxymethylindole (29 g) and manganese dioxide (66.7 g) in ethyl acetate (435 ml) was reflux for 2 hours. After filtration of the insoluble materials, the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography (10% ethyl acetate-toluene) to give 3-isopropyl-2-indolecarbaldehyde (24.2 g) as crystals.

Workup

  1. temperaturewas reflux for 2 hours
  2. filtrationAfter filtration of the insoluble materials
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (10% ethyl acetate-toluene)

Sources & evidence

ORD record
ord-28ea3fb961e64153930804765376e217
Source dataset
uspto-grants-1993_01
Patent number
US05180728

Reaction notes

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