Methanol → 5,10,15,20-Tetrakis[4-[2-(trimethylsilyl)ethynyl]phenyl]-21H,23H-porphine

HRID 2074041Notes

Reaction equation

HRID 2074041 reaction equation
[CH3:1][Si:2]([C:5]#[C:6][C:7]1[CH:14]=[CH:13][C:10](C=O)=[CH:9][CH:8]=1)([CH3:4])[CH3:3].N1[CH:19]=[CH:18][CH:17]=[CH:16]1.CO.[C:22]12[CH:45]=[C:43]3[N:44]=[C:40]([CH:41]=[CH:42]3)[CH:39]=[C:37]3[NH:38][C:34]([CH:35]=[CH:36]3)=[CH:33][C:31]3=[N:32][C:28]([CH:29]=[CH:30]3)=[CH:27][C:25]([NH:26]1)=[CH:24][CH:23]=2>C(O)(=O)CC>[CH3:1][Si:2]([C:16]#[C:17][C:18]1[CH:19]=[CH:8][C:7]([C:27]2[C:25]3[NH:26][C:22](=[CH:23][CH:24]=3)[C:45]([C:10]3[CH:13]=[CH:14][C:7]([C:6]#[C:5][Si:2]([CH3:3])([CH3:4])[CH3:1])=[CH:8][CH:9]=3)=[C:43]3[N:44]=[C:40]([CH:41]=[CH:42]3)[C:39]([C:10]3[CH:13]=[CH:14][C:7]([C:6]#[C:5][Si:2]([CH3:3])([CH3:4])[CH3:1])=[CH:8][CH:9]=3)=[C:37]3[NH:38][C:34]([CH:35]=[CH:36]3)=[C:33]([C:10]3[CH:9]=[CH:8][C:7]([C:6]#[C:5][Si:2]([CH3:1])([CH3:3])[CH3:4])=[CH:14][CH:13]=3)[C:31]3=[N:32][C:28]=2[CH:29]=[CH:30]3)=[CH:6][CH:5]=1)([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 8027PyrroleHCID 27716434-(Trimethylsilylethynyl)benzaldehydeHCID 13770524121H,22H-Porphine

Product 1

HCID 1354752945,10,15,20-Tetrakis[4-[2-(trimethylsilyl)ethynyl]phenyl]-21H,23H-porphineYield 12%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Conditions

Temperature
80 °C

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.

Workup

  1. temperatureThe temperature was subsequently increased
  2. temperatureat reflux for 4 hours
  3. waitwas then left
  4. customto crystallize
  5. filtrationThe medium was filtered over sintered glass
  6. washthe product was rinsed with methanol

Sources & evidence

ORD record
ord-0392d3f1401547a6a41861c5b70333d3
Source dataset
uspto-grants-2011_04
Patent number
US07919046B2

Reaction notes

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