Ethyl 5-(phenylmethoxy)-1H-indole-2-carboxylate → Ethyl 5-hydroxy-1H-indole-2-carboxylate

HRID 434015Notes

Reaction equation

HRID 434015 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15]CC1C=CC=CC=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]>C(O)C.CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([OH:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 95721Ethyl 5-(phenylmethoxy)-1H-indole-2-carboxylate

Product 1

HCID 90677Ethyl 5-hydroxy-1H-indole-2-carboxylateYield 100.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-benzyloxyindole-2-carboxylic acid ethyl ester (10 g, 34 mmol) in ethanol (250 mL) was treated with 10% Pd/C and hydrogenated under atmospheric pressure (double-walled balloon) for 20 h. The reaction mixture was diluted with EtOAc and filtered through Celite. Evaporation of the filtrate in vacuo gave the title compound as a tan solid (7 g, 99%). 1H NMR (400 MHz, CDCl3) δ 8.86 (br s, 1H), 7.29 (d, J=8.80 Hz, 1H), 7.11 (s, 1H), 7.06 (s, 1H), 6.94 (d, J=8.70 Hz, 1H), 4.83 (br s, 1H), 4.42 (q, J=7.09 Hz, 2H), 1.41 (t, J=7.08 Hz, 3H).

Workup

  1. filtrationfiltered through Celite
  2. customEvaporation of the filtrate in vacuo

Sources & evidence

ORD record
ord-e68a0f65428c436ea702d7d097cfbb81
Source dataset
uspto-grants-2003_12
Patent number
US06670388B1

Reaction notes

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