Acetone → 5,10,15,20-tetrakis(4-ethynylphenyl)-21H,23H-Porphine
Reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:32]3[NH:33][C:29](=[CH:30][CH:31]=3)[C:28]([C:34]3[CH:39]=[CH:38][C:37]([C:40]#[C:41][Si](C)(C)C)=[CH:36][CH:35]=3)=[C:27]3[N:46]=[C:24]([CH:25]=[CH:26]3)[C:23]([C:47]3[CH:52]=[CH:51][C:50]([C:53]#[C:54][Si](C)(C)C)=[CH:49][CH:48]=3)=[C:22]3[NH:59][C:19]([CH:20]=[CH:21]3)=[C:18]([C:60]3[CH:65]=[CH:64][C:63]([C:66]#[C:67][Si](C)(C)C)=[CH:62][CH:61]=3)[C:17]3=[N:72][C:14]=2[CH:15]=[CH:16]3)=[CH:9][CH:8]=1)(C)C.CC(C)=O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>C(Cl)(Cl)Cl.O1CCCC1>[C:53]([C:50]1[CH:49]=[CH:48][C:47]([C:23]2[C:22]3[NH:59][C:19](=[CH:20][CH:21]=3)[C:18]([C:60]3[CH:65]=[CH:64][C:63]([C:66]#[CH:67])=[CH:62][CH:61]=3)=[C:17]3[N:72]=[C:14]([CH:15]=[CH:16]3)[C:13]([C:10]3[CH:11]=[CH:12][C:7]([C:6]#[CH:5])=[CH:8][CH:9]=3)=[C:32]3[NH:33][C:29]([CH:30]=[CH:31]3)=[C:28]([C:34]3[CH:35]=[CH:36][C:37]([C:40]#[CH:41])=[CH:38][CH:39]=3)[C:27]3=[N:46][C:24]=2[CH:25]=[CH:26]3)=[CH:52][CH:51]=1)#[CH:54]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 700 mg (0.7 mmol) of protected TEPP (1) obtained above in 500 ml of a chloroform/tetrahydrofuran (THF) mixture (1/1 v/v) was cooled in a bath of liquid nitrogen and acetone to a temperature of between −30 and −50° C., and then a 1 mol/l solution of tetrabutylammonium fluoride (TBAF) in THF (259 mg, 0.99 mmol in 1 ml) was added to the reaction mixture, which was subsequently stirred for 20 hours. The rise in temperature was not controlled. The solvent was subsequently evaporated off and the deprotected porphyrin (2) was obtained in the form of a purple powder (747 mg, 1.05 mmol).
Workup
- customThe solvent was subsequently evaporated off
Sources & evidence
- ORD record
- ord-bae87a407f5a4e2f95a0b047939776bb
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07919046B2
Reaction notes
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