Reaction #2161223

Reaction equation

porphyrin

pyrrole

4-trimethylsilylethynylbenzaldehyde

methanol

→

porphyrin

Yield 12.0%

tetrakis(4-trimethylsilylethynylphenyl)porphyrin

Yield 12.0%

Solvents

propionic acid

Conditions

Workup

1. 1
   TemperatureThe temperature was subsequently increased
2. 2
   Temperatureat reflux for 4 hours
3. 3
   workup.WAITwas then left
4. 4
   Otherto crystallize
5. 5
   FiltrationThe medium was filtered over sintered glass
6. 6
   Washthe product was rinsed with methanol

Procedure

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.

Source