1-benzyl-5-benzyloxy-1H-indole → 1H-Indol-5-ol, 1-(phenylmethyl)-

HRID 854502Notes

Reaction equation

HRID 854502 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17]CC3C=CC=CC=3)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd]>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 120956361-benzyl-5-benzyloxy-1H-indole

Product 1

HCID 107754621H-Indol-5-ol, 1-(phenylmethyl)-Yield 63.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst2×

Procedure

A slurry of 0.98 g (3.12 mmol) 1-benzyl-5-benzyloxy-1H-indole, 0.20 g 20% Palladium on carbon, and 1.51 g (24 mmol) NH4CHO was heated to reflux with stirring for 3 days. The reaction was allowed to cool and an additional 0.20 g 20% Palladium on carbon and 1.33 g NH4CHO was added. The reaction was refluxed for an additional 24 hours upon which time the reaction was complete by TLC. The reaction was filtered through paper and concentrated. The residue was chromatographed on silica using 25–40% EtOAc-hexane to afford 0.44 g 1-benzyl-5-hydroxy-1H-indole as a solid.

Workup

  1. temperatureto reflux
  2. temperatureto cool
  3. temperatureThe reaction was refluxed for an additional 24 hours upon which time the reaction
  4. filtrationThe reaction was filtered through paper
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica using 25–40% EtOAc-hexane

Sources & evidence

ORD record
ord-74baa1afb8f545a0882bead2dbbf1aa2
Source dataset
uspto-grants-2007_08
Patent number
US07259182B2

Reaction notes

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