Ethyl 5-(Benzyloxy)indole-3-acetate → 5-hydroxy-1H-indole-3-acetic acid ethyl ester

HRID 1069646Notes

Reaction equation

HRID 1069646 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15]CC3C=CC=CC=3)[CH:13]=2)[NH:8][CH:7]=1)[CH3:2].[H][H]>C(O)C.[Ni]>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[NH:8][CH:7]=1)[CH3:2]

Participants

5

Reactant 2

HCID 10614830Ethyl 5-(Benzyloxy)indole-3-acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 145733265-hydroxy-1H-indole-3-acetic acid ethyl esterYield 128.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

5-Benzyloxy-1H-indole-3-acetic acid ethyl ester (8.1 g, 20.3 mmol) was hydrogenated in ethanol using 3 g of Raney Ni in 150 mL of ethanol at approximately 40 psi (2.76×105 Pa) of hydrogen. The catalyst was filtered and the filtrate concentrated at reduced pressure. The residue was chromatographed on silica gel eluting with a gradient, 30% ethyl acetate/hexane→50% ethyl acetate/hexane, to give 5.7 g (90% yield) of 5-hydroxy-1H-indole-3-acetic acid ethyl ester.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate concentrated at reduced pressure
  3. customThe residue was chromatographed on silica gel eluting with a gradient, 30% ethyl acetate/hexane→50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a00e71d08bbe4874b8f47dbbafc25eec
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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