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1-Bromooctane → 5,10,15-tris-(4-Hydroxy-phenyl)-20-(4-octyloxy-phenyl)-porphyrin

HRID 661809
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 661809
[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+].[CH2:59](Br)[CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66]>CN(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][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])=[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
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 1354380305,10,15,20-Tetrakis(4-hydroxyphenyl)porphyrin

Produkt 1

HCID 1360491895,10,15-tris-(4-Hydroxy-phenyl)-20-(4-octyloxy-phenyl)-porphyrin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel
2×

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

5,10,15,20-tetrakis-(4-Hydroxy-phenyl)-porphyrin (200 mg, 0.294 mmol) is dissolved and potassium carbonate (487 mg, 3.53 mmol, 12 eqv.) is suspended under argon in absolute DMF (50 mL) and the mixture is heated to 55° C. A solution of octyl bromide (35.8 μl, 0.206 mmol, 0.7 eqv.) in absolute DMF (10 mL) is added dropwise during 30 min. and the mixture is stirred at 55° C. for 2 h. The solvent is removed in vacuo at 50° C., water (80 mL) is added and the mixture is extracted with ethyl acetate (3×40 mL). The combined organic fraction is dried (Na2SO4) and the solvent evaporated. The residue is purified by chromatography on a column (300 g) of silica gel. Tetra-alkylated and tri-alkylated compounds are eluted with toluene:ethyl acetate (30:1 by vol.). The third fraction (di-substituted compound, trans-isomer) is eluted with toluene:ethyl acetate (15:1 by vol.). The fourth fraction (di-substituted compound, cis-isomer) is eluted with toluene:ethyl acetate (10:1 by vol.) and the desired product (mono-alkylated compound) is eluted with toluene:ethylacetate (5:1 by vol.). The solvent is removed under reduced pressure and the residue dried under high vacuum to give the product as a violet solid.

Aufarbeitung

  1. customThe solvent is removed in vacuo at 50° C.
  2. additionwater (80 mL) is added
  3. extractionthe mixture is extracted with ethyl acetate (3×40 mL)
  4. dry with materialThe combined organic fraction is dried (Na2SO4)
  5. customthe solvent evaporated
  6. customThe residue is purified by chromatography on a column (300 g) of silica gel
  7. washTetra-alkylated and tri-alkylated compounds are eluted with toluene:ethyl acetate (30:1 by vol.)
  8. washThe third fraction (di-substituted compound, trans-isomer) is eluted with toluene:ethyl acetate (15:1 by vol.)
  9. washThe fourth fraction (di-substituted compound, cis-isomer) is eluted with toluene:ethyl acetate (10:1 by vol.)
  10. washthe desired product (mono-alkylated compound) is eluted with toluene:ethylacetate (5:1 by vol.)
  11. customThe solvent is removed under reduced pressure
  12. customthe residue dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-120b0077c75d485b889193affd00d979
Quelldatensatz
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08084602B2

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