Reacción #2460315

Ecuación de reacción

methyl trifluoromethanesulfonate

Trans-4,4′-di[(4-n-butylphenyl)(3-benzylthiophenyl)amino]stilbene

→

trans-[3-((4-butylphenyl){4-[2-(4-{(4-butylphenyl)[3-((benzyl) methylsulfonio)phenyl]amino}phenyl)vinyl]phenyl}amino)phenyl]((benzyl)methyl)sulfonium triflate

Disolventes

dry ice acetone

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONTo this solution was added, via syringe
2. 2
   OtroAfter removal of some solvent under reduced pressure
3. 3
   workup.ADDITIONthe mixture was then poured into 20 ml of ether
4. 4
   OtroThe product was precipitated as a yellow solid, that
5. 5
   Lavadowas washed three times with ether
6. 6
   Otroisolated in 80.9% (1.07 g)
7. 7
   Otroyield

Procedimiento

Trans-4,4′-di[(4-n-butylphenyl)(3-benzylthiophenyl)amino]stilbene (16) (0.96 g, 1.103 mmol) was dissolved in 20 ml of dry methylene chloride and cooled at −78° C. in dry ice-acetone bath. To this solution was added, via syringe, methyl trifluoromethanesulfonate (276 μl, 2.437 mmol) and the mixture stirred for 30 min while the temperature was maintained at −78° C. The resultant mixture was then stirred two days at room temperature. After removal of some solvent under reduced pressure, the mixture was then poured into 20 ml of ether. The product was precipitated as a yellow solid, that was washed three times with ether and isolated in 80.9% (1.07 g) yield. 1H NMR (CD3COCD3, 500 MHz) δ ppm: 6.9-7.8 (m, 34 Ar—H, 2 ═CH), 5.27 (d, 2J=12.5 Hz, 2H, SCH2), 5.02 (d, 2J=12.5 Hz, 2H, SCH2), 3.53 (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)13C NMR (CD3COCD3, 125.7 MHz) δppm: 149.4, 145.6, 143.6, 139.9, 133.5, 131.8, 130.7, 130.1, 129.8, 129.3, 127.9, 127.7, 127.1, 126.5, 125.7, 124.5, 123.8, 123.4, 121.7, 51.0, 34.7, 33.5, 24.5, 22.1, 13.3. (One CF3 carbon was not observed).

Fuente