Indole → 7-(Benzyloxy)-1H-indole

HRID 54522

Reaction equation

HRID 54522 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([O:13][CH2:14][CH3:15])(=O)C>[Ni].C(O)C>[CH2:14]([O:13][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[NH:1][CH:2]=[CH:3]2)[C:15]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 798IndoleHCID 8857Ethyl Acetate

Product 1

HCID 2607987-(Benzyloxy)-1H-indole

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Wet Raney nickel is added in portions to a stirred refluxing solution of 7-(benzyloxy)-3-methylthio)indole (4.0 g, 14.9 mmol) in ethyl acetate (100 ml) and ethanol (60 ml) until all the starting material has been consumed (by RP HPLC). The mixture is filtered, the filtrate evaporated and the residue chromatographed on silica in ethyl acetate-hexane (1:8) to give a pale oil.

Workup

  1. customhas been consumed (by RP HPLC)
  2. filtrationThe mixture is filtered
  3. customthe filtrate evaporated
  4. customthe residue chromatographed on silica in ethyl acetate-hexane (1:8)
  5. customto give a pale oil

Sources & evidence

ORD record
ord-1390f576f6564c378bf76d8f0a770020
Source dataset
uspto-grants-1997_04
Patent number
US05622969

Linked notes

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