Reaktion #51773

Reaktionsgleichung

3-(4-tert-butyl-2-nitro-phenyl)-2-oxo-propionic acid ethyl ester

3-(4-tert-Butyl-2-nitro-phenyl)-2-oxo-propionic acid ethyl ester

EtOH

→

6-tert-Butyl-1H-indole-2-carboxylic acid ethyl ester

Lösungsmittel

AcOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Sonstigethe resulting mixture was evaporated
3. 3
   workup.ADDITIONTHF (100 mL) was added to the residue
4. 4
   Filtrationthe suspension was filtered on florisil
5. 5
   Wascheneluting with a large amount of THF
6. 6
   SonstigeThe solvents were evaporated
7. 7
   Sonstigethe residue was purified by flash silica gel chromatography (5%-30% EtOAc in hexanes as eluents)

Vorschrift

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).

Quelle