Pivalic anhydride → 21H,22H-Porphine

HRID 1613865Notes

Reaction equation

HRID 1613865 reaction equation
OC1C=CC=C(O)C=1[C:9]1[C:10]2[NH:14][C:13]([C:15](C3C(O)=CC=CC=3O)=[C:16]3[N:48]=[C:19]([C:20](C4C(O)=CC=CC=4O)=[C:21]4[NH:39][C:24](=[C:25](C5C(O)=CC=CC=5O)[C:26]5[CH:27]=[CH:28][C:29]=1[N:30]=5)[CH:23]=[CH:22]4)[CH:18]=[CH:17]3)=[CH:12][CH:11]=2.C(OC(=O)C(C)(C)C)(=O)C(C)(C)C>O1CCCC1.CN(C)C1C=CN=CC=1>[C:10]12[CH:9]=[C:29]3[N:30]=[C:26]([CH:27]=[CH:28]3)[CH:25]=[C:24]3[NH:39][C:21]([CH:22]=[CH:23]3)=[CH:20][C:19]3=[N:48][C:16]([CH:17]=[CH:18]3)=[CH:15][C:13]([NH:14]1)=[CH:12][CH:11]=2

Participants

5

Reactant 2

HCID 15234Pivalic anhydrideHCID 1354931875,10,15,20-Tetrakis(2,6-dihydroxyphenyl)porphyrin

Product 1

HCID 13770524121H,22H-Porphine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

On the other hand, a solution of 5,10,15,20-tetra(2',6'-dihydroxyphenyl)porphyrin in dry tetrahydrofuran is refluxed at the boiling point in an atmosphere of nitrogen, pivalic anhydride (40 times of the molar quantity) is added and then a small quantity of 4-dimethylaminopyridine is added. The mixture is refluxed for 10-24 hours. The reaction mixture is extracted by a suitable organic solvent (such as dichloromethane, chloroform, ether or the like), and the resulting solution is washed with dilute hydrochloric acid and with water. The organic layer is collected and the solvent is distilled away under reduced pressure. The residue obtained is purified by, for example, silica gel chromatography to obtain a porphyrin having no metal M (in the above process, the compound represented by H2T2,6 -dipivPP).

Workup

  1. additionis added
  2. temperatureThe mixture is refluxed for 10-24 hours
  3. extractionThe reaction mixture is extracted by a suitable organic solvent (such as dichloromethane, chloroform, ether
  4. washthe like), and the resulting solution is washed with dilute hydrochloric acid and with water
  5. customThe organic layer is collected
  6. distillationthe solvent is distilled away under reduced pressure
  7. customThe residue obtained
  8. customis purified by, for example, silica gel chromatography

Sources & evidence

ORD record
ord-138bb6497b8a408bb0059c86db328017
Source dataset
uspto-grants-1993_03
Patent number
US05194603

Reaction notes

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