Ethyl Acetate → 1-Benzyl-2-methyl-1H-indol-4-ol

HRID 1445916Notes

Reaction equation

HRID 1445916 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([O:17]CC3C=CC=CC=3)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C>[Pd].[Hg].CO>[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:17])[C:11]=2[CH:10]=[C:9]1[CH3:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 59170319HCID 59170319, compound

Product 1

HCID 107523601-Benzyl-2-methyl-1H-indol-4-olYield 49%

Reagents, catalysts & solvents 3

HCID 23931MercuryCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Benzyl-4-benzyloxy-2-methyl-1H-indole 2 (86 g, 0.263 mole) was dissolved with ethyl acetate (1.5 L) and methanol (300 mL). To the mixture 10% Pd/C wet (18 g) was added to the solution. The reaction was then subjected to H2 gas passed through a mercury bubbler at room temperature and 1 atm. The mixture was left to stir for 6 h. The reaction mixture was filtered through Celite and concentrated. The residue was purified by column chromatography (3:1 Hexane:EtOAc) to afford 3 (30 g, 49%) as a cream solid.

Workup

  1. waitThe mixture was left
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (3:1 Hexane:EtOAc)

Sources & evidence

ORD record
ord-032265eea960432880ae843cdf552b3d
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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