Water → 2,5-Di([1,1'-biphenyl]-3-yl)-3,4-bis(4-chlorophenyl)cyclopenta-2,4-dienone

HRID 57310

Reaktionsgleichung

Reaktionsgleichung von HRID 57310
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=O)=O)=[CH:4][CH:3]=1.[C:19]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][C:26](=[O:40])[CH2:27][C:28]2[CH:29]=[C:30]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:31]=[CH:32][CH:33]=2)[CH:20]=1.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C(O)(C)(C)C>[C:30]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:31]=[CH:32][CH:33]=[C:28]([C:27]2[C:26](=[O:40])[C:25]([C:21]3[CH:20]=[C:19]([C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)[CH:24]=[CH:23][CH:22]=3)=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[C:10]=2[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH:29]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 189461,2-Ethanedione, 1,2-bis(4-chlorophenyl)-HCID 2723671Tetrabutylammonium HydroxideHCID 577828671,3-Di(biphenyl-3-yl)propan-2-one

Produkt 1

HCID 895341922,5-Di([1,1'-biphenyl]-3-yl)-3,4-bis(4-chlorophenyl)cyclopenta-2,4-dienoneAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a degassed solution of 940 mg of 4,4′-dichlorobenzil (3.37 mmol) and 1.22 g of 1,3-di(biphenyl-3-yl)propan-2-one (7, 3.37 mmol) in 20 ml of tert-butanol was added, at 80° C., a methanolic tetrabutylammonium hydroxide solution (1M, 1.7 ml, 1.7 mmol). The reaction solution was stirred at 80° C. for 20 minutes, and the reaction then stopped by adding water. The mixture was extracted three times with dichloromethane and the collected organic phases were washed with saturated sodium chloride solution and dried over magnesium sulfate, before the solvent was distilled off under reduced pressure. The crude product was purified by column chromatography (silica gel, eluent: hexane with 20% DCM) and gave 1.56 g of the tetraarylcyclopentadienone 8b as a pale violet solid (77%, 2.58 mmol). Elemental analysis measured: C 81.3; H 3.3% (calculated for C41H26Cl2O: C, 81.3; H, 4.3%); 1H NMR (700 MHz, d8-THF) δ=7.52 (s, 2H, CH), 7.50 (d, J=7.8 Hz, 2H, CH), 7.42 (d, J=7.2 Hz, 4H, CH), 7.36 (t, J=7.7 Hz, 4H, CH), 7.32 (m, 6H, CH), 7.27 (t, J=7.3 Hz, 2H, CH), 7.23 (d, J=7.8 Hz, 2H, CH), 7.06 (d, J=8.5 Hz, 4H, CH); 13C NMR (175 MHz, d8-THF) δ=199.86, 154.28, 141.91, 141.82, 135.61, 133.14, 132.14, 132.10, 129.98, 129.90, 129.70, 129.69, 129.52, 128.27, 127.78, 127.20, 126.73; MS (MALDI-TOF): m/z (%): 604.6 (100) [M+] (calculated for C41H26Cl2: 604.1); Rf (hexane with 10% ethyl acetate)=0.47.

Aufarbeitung

  1. customthe reaction
  2. extractionThe mixture was extracted three times with dichloromethane
  3. washthe collected organic phases were washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate, before the solvent
  5. distillationwas distilled off under reduced pressure
  6. customThe crude product was purified by column chromatography (silica gel, eluent: hexane with 20% DCM)

Quellen und Nachweise

ORD-Eintrag
ord-dedc7ad8277944c88f5bde5de79f7c3a
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434619B2

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