Potassium Carbonate → 5,10,15-tris-(4-Hydroxy-phenyl)-20-(4-undecyloxy-phenyl)-porphyrin

HRID 1296326Notes

Reaction equation

HRID 1296326 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[NH:13][C:12]([C:14]([C:46]4[CH:51]=[CH:50][C:49]([OH:52])=[CH:48][CH:47]=4)=[C:15]4[N:45]=[C:18]([C:19]([C:38]5[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=5)=[C:20]5[NH:37][C:23](=[C:24]([C:30]6[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=6)[C:25]6[CH:26]=[CH:27][C:28]=2[N:29]=6)[CH:22]=[CH:21]5)[CH:17]=[CH:16]4)=[CH:11][CH:10]=3)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH3:70]>CN(C=O)C.ClCCl.C1(C)C=CC=CC=1.C(O)C>[OH:52][C:49]1[CH:48]=[CH:47][C:46]([C:14]2[C:12]3[NH:13][C:9]([C:8]([C:5]4[CH:6]=[CH:7][C:2]([O:1][CH2:70][CH2:69][CH2:68][CH2:67][CH2:66][CH2:65][CH2:64][CH2:63][CH2:62][CH2:61][CH3:60])=[CH:3][CH:4]=4)=[C:28]4[N:29]=[C:25]([C:24]([C:30]5[CH:31]=[CH:32][C:33]([OH:36])=[CH:34][CH:35]=5)=[C:23]5[NH:37][C:20](=[C:19]([C:38]6[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=6)[C:18]6[CH:17]=[CH:16][C:15]=2[N:45]=6)[CH:21]=[CH:22]5)[CH:26]=[CH:27]4)=[CH:10][CH:11]=3)=[CH:51][CH:50]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 127441-BromoundecaneHCID 1354380305,10,15,20-Tetrakis(4-hydroxyphenyl)porphyrin

Product 1

HCID 1360491885,10,15-tris-(4-Hydroxy-phenyl)-20-(4-undecyloxy-phenyl)-porphyrin

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolventHCID 21863594Toluene ethanolSolvent

Procedure

To a vigorously-stirred suspension of 5,10,15,20-tetrakis-(4-hydroxy-phenyl)-porphyrin (400 mg, 0.59 mmol) and K2CO3 (1.0 g, 7.1 mmol) in DMF (75 mL), a solution of 1-bromoundecane (0.1 mL, 0.45 mmol) in DMF (10 mL) is added dropwise at 50° C. during 30 mins and the mixture is stirred at the same temperature for 1.5 h. After removal by filtration of K2CO3 and removal under reduced pressure of DMF, the residue obtained is dissolved in dichloromethane (200 mL), washed with water (3×150 mL) and the solution dried (Na2SO4). The solvent is evaporated under reduced pressure and the residue obtained is dissolved in toluene:ethanol (5:1 by vol., ca. 10 mL) and purified by chromatography using a column (5×50 cm) of silica gel (Merck 60). The column is eluted with toluene followed by toluene:ethyl acetate (2:1 by vol.) and the desired material recovered by evaporation of solvent from the appropriate fractions is dried under high vacuum. The product is obtained as violet crystals.

Workup

  1. customAfter removal
  2. filtrationby filtration of K2CO3 and removal under reduced pressure of DMF
  3. customthe residue obtained
  4. washwashed with water (3×150 mL)
  5. dry with materialthe solution dried (Na2SO4)
  6. customThe solvent is evaporated under reduced pressure
  7. customthe residue obtained
  8. custompurified by chromatography
  9. washThe column is eluted with toluene
  10. customthe desired material recovered by evaporation of solvent from the appropriate fractions
  11. customis dried under high vacuum
  12. customThe product is obtained as violet crystals

Sources & evidence

ORD record
ord-4adac1373ddf41dbb6c8e356d0891770
Source dataset
uspto-grants-2007_07
Patent number
US07244841B2

Reaction notes

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