Ethyl 4-benzyloxy-1-methylindole-2-carboxylate → Ethyl 4-hydroxy-1-methyl-1H-indole-2-carboxylate

HRID 749302Notes

Reaction equation

HRID 749302 reaction equation
C([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:13]2[CH3:18])C1C=CC=CC=1>CCO.[Pd]>[OH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:13]2[CH3:18]

Participants

4

Reactant 1

HCID 22054863Ethyl 4-benzyloxy-1-methylindole-2-carboxylate

Product 1

HCID 10130663Ethyl 4-hydroxy-1-methyl-1H-indole-2-carboxylateYield 45.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 10% Pd/C (0.13 g) in EtOH (250 mL) was added ethyl 4-benzyloxy-1-methyl-1H-indole-2-carboxylate (1.33 g) and the suspension was shaken overnight under a hydrogen pressure of 3 atmospheres at room temperature. The residue left on evaporation of the filtered reaction mixture was chromatographed over silica gel with a mixture of EtOAc and hexane to give 0.43 g of the title compound. MS ES (M++H)=220.

Workup

  1. waitThe residue left on evaporation of the filtered reaction mixture
  2. customwas chromatographed over silica gel with a mixture of EtOAc and hexane

Sources & evidence

ORD record
ord-559ba62943ad47d286b68ce16e0de936
Source dataset
uspto-grants-2008_07
Patent number
US07402604B2

Reaction notes

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