Reaktion #2161223

ord-0392d3f1401547a6a41861c5b70333d3

Reaktionsgleichung

C1=Cc2cc3ccc(cc4nc(cc5ccc(cc1n2)[nH]5)C=C4)[nH]3
porphyrin
c1cc[nH]c1
pyrrole
C[Si](C)(C)C#Cc1ccc(C=O)cc1
4-trimethylsilylethynylbenzaldehyde
CO
methanol
C[Si](C)(C)C#Cc1ccc(-c2c3nc(c(-c4ccc(C#C[Si](C)(C)C)cc4)c4ccc([nH]4)c(-c4ccc(C#C[Si](C)(C)C)cc4)c4nc(c(-c5ccc(C#C[Si](C)(C)C)cc5)c5ccc2[nH]5)C=C4)C=C3)cc1
porphyrin
Ausbeute 12.0%
C[Si](C)(C)C#Cc1ccc(-c2c3nc(c(-c4ccc(C#C[Si](C)(C)C)cc4)c4ccc([nH]4)c(-c4ccc(C#C[Si](C)(C)C)cc4)c4nc(c(-c5ccc(C#C[Si](C)(C)C)cc5)c5ccc2[nH]5)C=C4)C=C3)cc1
tetrakis(4-trimethylsilylethynylphenyl)porphyrin
Ausbeute 12.0%

Lösungsmittel

Reaktionsbedingungen

Temperatur
80°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe temperature was subsequently increased
  2. 2
    Temperaturat reflux for 4 hours
  3. 3
    workup.WAITwas then left
  4. 4
    Sonstigeto crystallize
  5. 5
    FiltrationThe medium was filtered over sintered glass
  6. 6
    Waschenthe product was rinsed with methanol

Vorschrift

5.02 g of 4-trimethylsilylethynylbenzaldehyde (25 mmol) were dissolved in 210 ml of propionic acid and then heated to 80° C. 1.72 ml of pyrrole (25 mmol) were subsequently added portionwise over a period of one hour. The temperature was subsequently increased and the mixture was kept at reflux for 4 hours. After a return to ambient temperature, 75 ml of methanol were added to the reaction medium, which was then left to stand for 14 hours in order for the porphyrin to crystallize. The medium was filtered over sintered glass and the product was rinsed with methanol. 2.87 g (3 mmol; yield 12%) of the expected porphyrin (1) were obtained in the form of a purple powder.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07919046B2uspto-grants-2011_04