Pivalic acid → HCID 86746623, compound

HRID 1613867Notes

Reaction equation

HRID 1613867 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9]1[C:10]2[NH:14][C:13]([C:15]([C:49]3[C:54]([OH:55])=[CH:53][CH:52]=[CH:51][C:50]=3[OH:56])=[C:16]3[N:48]=[C:19]([C:20]([C:40]4[C:45]([OH:46])=[CH:44][CH:43]=[CH:42][C:41]=4[OH:47])=[C:21]4[NH:39][C:24](=[C:25]([C:31]5[C:36]([OH:37])=[CH:35][CH:34]=[CH:33][C:32]=5[OH:38])[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:57]([OH:63])(=O)[C:58]([CH3:61])([CH3:60])[CH3:59]>O1CCCC1.CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[C:57]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:57](=[O:63])[C:58]([CH3:61])([CH3:60])[CH3:59])[C:3]=1[C:9]1[C:10]2[NH:14][C:13]([C:15]([C:49]3[C:50]([O:56][C:57](=[O:63])[C:58]([CH3:61])([CH3:60])[CH3:59])=[CH:51][CH:52]=[CH:53][C:54]=3[O:55][C:57](=[O:63])[C:58]([CH3:61])([CH3:60])[CH3:59])=[C:16]3[N:48]=[C:19]([C:20]([C:40]4[C:45]([O:46][C:57](=[O:63])[C:58]([CH3:61])([CH3:60])[CH3:59])=[CH:44][CH:43]=[CH:42][C:41]=4[O:47][C:57](=[O:63])[C:58]([CH3:61])([CH3:60])[CH3:59])=[C:21]4[NH:39][C:24](=[C:25]([C:31]5[C:32]([O:38][C:57](=[O:63])[C:58]([CH3:61])([CH3:60])[CH3:59])=[CH:33][CH:34]=[CH:35][C:36]=5[O:37][C:57](=[O:63])[C:58]([CH3:61])([CH3:60])[CH3:59])[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)(=[O:63])[C:58]([CH3:61])([CH3:60])[CH3:59]

Participants

6

Reactant 2

HCID 6417Pivalic acidHCID 1354931875,10,15,20-Tetrakis(2,6-dihydroxyphenyl)porphyrin

Product 1

HCID 86746623HCID 86746623, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

50 ml of a solution of 1.0 g of 5,10,15,20-tetra(2',6'-dihydroxyphenyl)porphyrin in dry tetrahydrofuran was refluxed at the boiling point in an atmosphere of nitrogen. 5.0 g of anhydrous pivalic acid and then 0.17 g of 4-dimethylaminopyridine were added to the solution, and the mixture was heated under reflux for about 20 hours. The reaction solution was evaporated and the residue obtained was dissolved in 250 ml of chloroform. The chloroform solution was washed with dilute hydrochloric acid and with water. The solution was dehydrated by using anhydrous sodium sulfate and filtered, and the filtrate was evaporated to dryness. The residue obtained was fractionated and purified by chromatography on a column of silica gel (chloroform / ether (10/1) (volume/volume)). The object fractionated was collected and evaporated to dryness under reduced pressure. Thus, 5,10,15,20-tetra(2',6'-dipivaloyloxyphenyl)porphyrin was obtained as violet needle crystals. Yield: 1.15g (60%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for about 20 hours
  3. customThe reaction solution was evaporated
  4. customthe residue obtained
  5. washThe chloroform solution was washed with dilute hydrochloric acid and with water
  6. filtrationfiltered
  7. customthe filtrate was evaporated to dryness
  8. customThe residue obtained
  9. custompurified by chromatography on a column of silica gel (chloroform / ether (10/1) (volume/volume))
  10. customThe object fractionated was collected
  11. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9d0619a3d27e4b11b6d3c7f694216d5f
Source dataset
uspto-grants-1993_03
Patent number
US05194603

Reaction notes

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