Water → HCID 136426468, compound

HRID 987355Notes

Reaction equation

HRID 987355 reaction equation
CS([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:20]3[NH:24][C:23]([C:25]([C:97]4[CH:102]=[C:101]([O:103][CH2:104][CH2:105][CH2:106][CH2:107][CH2:108][CH3:109])[C:100]([O:110][CH2:111][CH2:112][CH2:113][CH2:114][CH2:115][CH3:116])=[C:99]([O:117][CH2:118][CH2:119][CH2:120][CH2:121][CH2:122][CH3:123])[CH:98]=4)=[C:26]4[N:96]=[C:29]([C:30]([C:69]5[CH:74]=[C:73]([O:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH3:81])[C:72]([O:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH3:88])=[C:71]([O:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH3:95])[CH:70]=5)=[C:31]5[NH:68][C:34](=[C:35]([C:41]6[CH:46]=[C:45]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[C:44]([O:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])=[C:43]([O:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67])[CH:42]=6)[C:36]6[CH:37]=[CH:38][C:39]=2[N:40]=6)[CH:33]=[CH:32]5)[CH:28]=[CH:27]4)=[CH:22][CH:21]=3)=[CH:15][CH:14]=1)(=O)=O.[C:124]([O-])(=O)[CH:125]=[CH:126][CH3:127].[Na+].O>C1COCC1>[CH2:127]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:20]3[NH:24][C:23]([C:25]([C:97]4[CH:102]=[C:101]([O:103][CH2:104][CH2:105][CH2:106][CH2:107][CH2:108][CH3:109])[C:100]([O:110][CH2:111][CH2:112][CH2:113][CH2:114][CH2:115][CH3:116])=[C:99]([O:117][CH2:118][CH2:119][CH2:120][CH2:121][CH2:122][CH3:123])[CH:98]=4)=[C:26]4[N:96]=[C:29]([C:30]([C:69]5[CH:74]=[C:73]([O:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH3:81])[C:72]([O:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH3:88])=[C:71]([O:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH3:95])[CH:70]=5)=[C:31]5[NH:68][C:34](=[C:35]([C:41]6[CH:46]=[C:45]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[C:44]([O:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])=[C:43]([O:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67])[CH:42]=6)[C:36]6[CH:37]=[CH:38][C:39]=2[N:40]=6)[CH:33]=[CH:32]5)[CH:28]=[CH:27]4)=[CH:22][CH:21]=3)=[CH:15][CH:14]=1)[CH2:126][CH:125]=[CH2:124]

Participants

5

Reactant 3

HCID 962WaterHCID 74083674HCID 74083674, compoundHCID 136426574HCID 136426574, compound

Product 1

HCID 136426468HCID 136426468, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-[4-(6-Methanesulfonyloxy-hexyloxy)-phenyl]-10,15,20-tris3,4,5-trihexyloxy-phenyl)-porphyrin (573mg, 0.33mmol, see Example 43) was heated to reflux in dry THF (20 ml). A solution of sodium butenoate (NaH (excess) in 3-buten-1-ol (1 equiv.)) was added causing the reaction mixture to turn deep green. The reaction was heated at reflux until the reaction was complete (ca. 3-5 hours). The mixture was cooled, water was added and the solution was extracted with diethyl ether. The organic phase was washed with brine, dried over MgSO4, filtered and the filtrate evaporated under reduced pressure. Column chromatography on silica gel with petroleum ether (b.p. 40-60° C.):THF (10:1 by volume) yielded the title compound.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux until the reaction
  3. custom(ca. 3-5 hours)
  4. temperatureThe mixture was cooled
  5. extractionthe solution was extracted with diethyl ether
  6. washThe organic phase was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-3ab4ab4e339e4f518091a6fe9698c400
Source dataset
uspto-grants-2003_10
Patent number
US06630128B1

Reaction notes

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