Reacción #2460326

Ecuación de reacción

p-butoxybenzaldehyde

tetraethyl 2-bromo-α,α′-p-xylenebisphosphonate

KOtBu

→

2-bromo-E,E-1,4-bis[p-n-butoxystyryl]benzene

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter 2 hours the reaction was quenched by addition of 70 ml of methanol
2. 2
   FiltraciónA light yellow solid was collected by filtration
3. 3
   Lavadowashed three times with methanol
4. 4
   Otroto afford NMR-pure product in 2.36 g (84.5%)
5. 5
   Otroyield

Procedimiento

To a solution of p-butoxybenzaldehyde (71) (2.0 g, 11.2 mmol) and tetraethyl 2-bromo-α,α′-p-xylenebisphosphonate (70) (2.55 g,. 5.5 mmol) in dry THF (70 ml) at 0° C. was added 12 ml of 1 M solution of KOtBu in THF. After 2 hours the reaction was quenched by addition of 70 ml of methanol. A light yellow solid was collected by filtration and washed three times with methanol to afford NMR-pure product in 2.36 g (84.5%) yield.1H NMR (CDCl3, 500 MHz) δppm: 7.70 (s, 1H), 7.62 (d, J=8.5 Hz, 1H), 7.47 (d, J=8.0 Hz, 2H), 7.44 (d, J=8.5 Hz, 2H), 7.4 (d, J=7.5 Hz, 1H), 7.32 (d, J=16.5 Hz, 1H, ═CH), 7.06 (d, J=16.5 Hz, 1H, ═C), 7.01 (d, J=16.0 Hz, 1H, ═CH), 6.85-6.95 (m, 5H, 4 Ar—H, 1 ═CH), 4.0 (m, 4H, CH2), 1.80 (m, 4H, CH2), 1.52 (m, 4H, CH2), 1.0 (t, J=7.5 Hz, 6H, CH3)13C NMR (CDCl3, 125.7 MHz) δppm: 159.1, 138.1, 135.7, 130.5, 130.4, 129.7, 129.4, 129.2, 128.0, 127.8, 126.2, 125.2, 124.7, 124.5, 124.3, 114.7, 67.7, 31.3, 19.2, 13.9.

Fuente