1-Bromodecane → 5,10,15-tris-(4-Hydroxy-phenyl)-20-(4-decyloxy-phenyl)-porphyrin

HRID 661807Notes

Reaction equation

HRID 661807 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][CH3:69]>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][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH3:69])=[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

5

Reactant 3

HCID 81731-BromodecaneHCID 11430Potassium CarbonateHCID 1354380305,10,15,20-Tetrakis(4-hydroxyphenyl)porphyrin

Product 1

HCID 1359160635,10,15-tris-(4-Hydroxy-phenyl)-20-(4-decyloxy-phenyl)-porphyrin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5,10,15,20-tetrakis-(4-Hydroxy-phenyl)-porphyrin (100 mg, 0.15 mmol) is dissolved and K2CO3 (230 mg) is suspended in DMF (30 mL). To the vigorously stirred reaction mixture a solution of 1-bromodecane (0.016 mL, 0.11 mmol) in DMF (10 mL) is added dropwise at 70° C. during 30 mins and the mixture is stirred for 1.5 h. After evaporation of solvent, the residue is dissolved in toluene:ethanol (1:1 by vol., ca. 3 mL) and purified by chromatography on a column (150 g) of silica gel (Merck 60) using toluene as eluent. After elution of the first 3 fractions, the column is eluted with toluene:ethyl acetate (2:1 by vol.) and the 5th fraction eluted is collected, the solvent removed and the residue dried under high vacuum to give the product as violet crystals.

Workup

  1. additionis added dropwise at 70° C. during 30 mins
  2. customAfter evaporation of solvent
  3. dissolutionthe residue is dissolved in toluene:ethanol (1:1 by vol., ca. 3 mL)
  4. custompurified by chromatography on a column (150 g) of silica gel (Merck 60)
  5. washAfter elution of the first 3 fractions
  6. washthe column is eluted with toluene:ethyl acetate (2:1 by vol.)
  7. washthe 5th fraction eluted
  8. customis collected
  9. customthe solvent removed
  10. customthe residue dried under high vacuum

Sources & evidence

ORD record
ord-d78f0b03ab9c41e79d797c1537823fed
Source dataset
uspto-grants-2011_12
Patent number
US08084602B2

Reaction notes

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