Reacción #2460318

ord-1ccfa20b304041a5a551b2cc18a61144

Ecuación de reacción

[F][Sb-]([F])([F])([F])([F])[F].[Na+]
sodium hexafluoroantimonate
CCCCc1ccc(N(c2ccc(/C=C/c3ccc(N(c4ccc(CCCC)cc4)c4cccc([SH+]CCc5ccccc5)c4)cc3)cc2)c2cccc([SH+]CCc3ccccc3)c2)cc1.O=S(=O)([O-])C(F)(F)F.O=S(=O)([O-])C(F)(F)F
trans-[3-((4-butylphenyl){4-[2-(4-{(4-butylphenyl)[3-((benzyl)methylsulfonio)phenyl]amino}phenyl)vinyl]phenyl}amino)phenyl]((benzyl)methyl)sulfonium triflate
CCCCc1ccc(N(c2ccc(/C=C/c3ccc(N(c4ccc(CCCC)cc4)c4cccc([SH+]CCc5ccccc5)c4)cc3)cc2)c2cccc([SH+]CCc3ccccc3)c2)cc1.O=S(=O)([O-])C(F)(F)F.O=S(=O)([O-])C(F)(F)F
trans-[3-((4-butylphenyl){4-[2-(4-{(4-butylphenyl)[3-((benzyl) methylsulfonio)phenyl]amino}phenyl)vinyl]phenyl}amino)phenyl]((benzyl)methyl)sulfonium triflate
CCCCc1ccc(N(c2ccc(/C=C/c3ccc(N(c4ccc(CCCC)cc4)c4cccc([SH+]CCc5ccccc5)c4)cc3)cc2)c2cccc([SH+]CCc3ccccc3)c2)cc1.[F][Sb-]([F])([F])([F])([F])[F].[F][Sb-]([F])([F])([F])([F])[F]
trans-[3-((4-butylphenyl){4-[2-(4-{(4-butylphenyl)[3-((benzyl)methylsulfonio)phenyl]amino}phenyl)vinyl]phenyl}amino)phenyl]((benzyl)methyl)sulfonium hexafluoroantimonate
Rendimiento 83.2%

Disolventes

Condiciones de reacción

Temperatura
0°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrothe yellow oil that formed
  2. 2
    FiltraciónThe yellow solid was collected by filtration
  3. 3
    Lavadowashed four times with water and three times with ether
  4. 4
    OtroNMR-pure product was obtained without further purification in 83.2% yield (0.85 g)

Procedimiento

trans-[3-((4-butylphenyl){4-[2-(4-{(4-butylphenyl)[3-((benzyl)methylsulfonio)phenyl]amino}phenyl)vinyl]phenyl}amino)phenyl]((benzyl)methyl)sulfonium triflate (20) (0.85 g 0.81 mmol) was dissolved in acetone (10 ml). To this solution was added 10 ml of an aqueous solution of sodium hexafluoroantimonate (0.84 g, 3.25 mmol). The resultant mixture was stirred two days with slow evaporation of acetone in the dark at room temperature. The mixture was allowed to cool at 0° C., the yellow oil that formed solidified. The yellow solid was collected by filtration and washed four times with water and three times with ether. NMR-pure product was obtained without further purification in 83.2% yield (0.85 g). 1H NMR (CD3COCD3, 500 MHz) δ ppm: 6.9-7.7 (m, 36H, 34 Ar—H, 2 ═CH), 5.27 (d, 2J=12.5 Hz, 2H, SCH2), 5.02 (d, 2J=12.5 Hz, 2H, SCH2), 3.52 (s, 6H, CH3), 2.63 (t, J=7.7 Hz, CH2, 4H), 1.61 (m, CH2, 4H), 1.36 (m, CH2, 4H), 0.95 (t, J=7.2 Hz, CH3, 6H)13 C NMR (CD3COCD3, 125.7 MHz) δppm: 149.3, 145.6, 143.5, 139.9, 133.5, 131.9, 130.7, 130.0, 129.8, 129.3, 127.9, 127.7, 127.1, 126.5, 125.6, 124.5, 123.8, 123.4, 121.7, 51.0, 34.7, 33.5, 24.5, 22.1, 13.3.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07459106B2uspto-grants-2008_12