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

HRID 1130

Reaktionsgleichung

Reaktionsgleichung von HRID 1130
[CH3:1][N:2]1[CH:6]=[C:5](I)[CH:4]=[C:3]1[C:8]([O:10][CH3:11])=[O:9].[CH3:12][C:13]1([CH3:32])[CH2:26][CH2:25][C:24]([CH3:28])([CH3:27])[C:23]2[CH:22]=[C:21]3[C:16]([CH:17]=[CH:18][C:19](B(O)O)=[CH:20]3)=[CH:15][C:14]1=2.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH3:1][N:2]1[CH:6]=[C:5]([C:19]2[CH:18]=[CH:17][C:16]3[C:21](=[CH:22][C:23]4[C:24]([CH3:28])([CH3:27])[CH2:25][CH2:26][C:13]([CH3:32])([CH3:12])[C:14]=4[CH:15]=3)[CH:20]=2)[CH:4]=[C:3]1[C:8]([O:10][CH3:11])=[O:9]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 196946765,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-anthrylboronic acidHCID 21826247methyl 4-iodo-1-methyl-1H-pyrrole-2-carboxylate

Produkt 1

HCID 19694675methyl N-methyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)-2-pyrrolecarboxylateAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 8 hours
  3. customThe reaction medium was evaporated to dryness
  4. customethyl ether, the organic phase decanted
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by chromatography on a silica column
  8. washeluted with a mixture of dichloromethane and hexane (80/20)

Quellen und Nachweise

ORD-Eintrag
ord-205c29c6463642c4a3ef2726db5ff6fc
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723499

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