반응 #85588

반응 방정식

water

4,4′-dichlorobenzil

1,3-di(biphenyl-3-yl)propan-2-one

tetrabutylammonium hydroxide

→

tetraarylcyclopentadienone

수율 77.0%

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

수율 77.0%

용매

tert-butanol

반응 조건

후처리

1. 1
   기타the reaction
2. 2
   추출The mixture was extracted three times with dichloromethane
3. 3
   세척the collected organic phases were washed with saturated sodium chloride solution
4. 4
   건조dried over magnesium sulfate, before the solvent
5. 5
   workup.DISTILLATIONwas distilled off under reduced pressure
6. 6
   기타The crude product was purified by column chromatography (silica gel, eluent: hexane with 20% DCM)

실험 절차

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.

출처