Reaktion #1226

Reaktionsgleichung

5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthrylboronic acid

potassium carbonate

methyl N-methyl-4-iodo-2-pyrrolecarboxylate

→

methyl N-methyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)-2-pyrrolecarboxylate

Ausbeute 47.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated
2. 2
   Temperaturat reflux for 8 hours
3. 3
   SonstigeThe reaction medium was evaporated to dryness
4. 4
   Sonstigeethyl ether, the organic phase decanted
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue was purified by chromatography on a silica column
8. 8
   Wascheneluted with a mixture of dichloromethane and hexane (80/20)

Vorschrift

231 mg (0.2 mml) of tetrakis-(triphenylphosphine)palladium (0), 50 ml of toluene and 1.75 g (6.6 mmol) of methyl N-methyl-4-iodo-2-pyrrolecarboxylate were introduced into a three-necked flask and under a nitrogen stream and the mixture was stirred at room temperature for 20 minutes. 2.8 g (10 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthrylboronic acid and 6.6 ml of an aqueous potassium carbonate solution (2N) were then added and the mixture was heated at reflux for 8 hours. The reaction medium was evaporated to dryness, taken up in water and ethyl ether, the organic phase decanted, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on a silica column eluted with a mixture of dichloromethane and hexane (80/20). 840 mg (47%) of methyl N-methyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)-2-pyrrolecarboxylate were obtained.

Quelle