تفاعل #2161223

ord-0392d3f1401547a6a41861c5b70333d3

معادلة التفاعل

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
المردود 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
المردود 12.0%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

درجة الحرارة
80°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةThe temperature was subsequently increased
  2. 2
    درجة الحرارةat reflux for 4 hours
  3. 3
    workup.WAITwas then left
  4. 4
    أخرىto crystallize
  5. 5
    ترشيحThe medium was filtered over sintered glass
  6. 6
    غسيلthe product was rinsed with methanol

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07919046B2uspto-grants-2011_04