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

HRID 2243165Notes

Reaction equation

HRID 2243165 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-02692ba06e86407c8ced4975a926086f
Source dataset
uspto-grants-2010_03
Patent number
US07674818B2

Reaction notes

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