Ethanol → Ethyl 6-(tert-Butyl)indole-2-carboxylate

HRID 23495Notes

Reaction equation

HRID 23495 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5](=O)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][C:8]=1[N+:17]([O-])=O)[CH3:2].CCO>[Fe].CC(O)=O>[CH2:1]([O:3][C:4]([C:5]1[NH:17][C:8]2[C:7]([CH:6]=1)=[CH:12][CH:11]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:9]=2)=[O:21])[CH3:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 542454313-(4-tert-Butyl-2-nitro-phenyl)-2-oxo-propionic Acid Ethyl Ester

Product 1

HCID 43415424Ethyl 6-(tert-Butyl)indole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 3-(4-tert-butyl-2-nitro-phenyl)-2-oxo-propionic acid ethyl ester (prepared in Example XX; 9.1 g, 31 mmol), iron powder (15.3 g, 274 mmol). EtOH (70 mL), and glacial AcOH (70 mL) was refluxed for 2 hours. After cooling, the resulting mixture was evaporated. THF (100 mL) was added to the residue, and the suspension was filtered on florisil, eluting with a large amount of THF. The solvents were evaporated, and the residue was purified by flash silica gel chromatography (5%-30% EtOAc in hexanes as eluents). MS(APCI): 246 (M+H).

Workup

  1. temperatureAfter cooling
  2. customthe resulting mixture was evaporated
  3. additionTHF (100 mL) was added to the residue
  4. filtrationthe suspension was filtered on florisil
  5. washeluting with a large amount of THF
  6. customThe solvents were evaporated
  7. customthe residue was purified by flash silica gel chromatography (5%-30% EtOAc in hexanes as eluents)

Sources & evidence

ORD record
ord-2ad5bcb5d9b74404b3b823596067c11e
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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