反応 #2460325

反応方程式

p-butoxybenzaldehyde

tetraethyl 2,5-dibromo-α,α′-p-xylenebisphosphonate

KOtBu

→

2,5-dibromo-E,E-1,4-bis[p-n-butoxystyryl]benzene

溶媒

THF

THF

反応条件

後処理

1. 1
   その他After 2 hours the reaction was quenched by addition of 20 ml of methanol
2. 2
   ろ過A yellow solid was collected by filtration
3. 3
   洗浄washed three times with methanol
4. 4
   その他to afford NMR-pure product in 0.92 g (82.9%)
5. 5
   その他yield

実験手順

To a solution of p-butoxybenzaldehyde (71) (0.7 g, 3.95 mmol) and tetraethyl 2,5-dibromo-α,α′-p-xylenebisphosphonate (69) (1.02 g, 1.90 mmol) in dry THF (25 ml) at 0° C. was added 4 ml of 1 M solution of KOtBu in THF. After 2 hours the reaction was quenched by addition of 20 ml of methanol. A yellow solid was collected by filtration and washed three times with methanol to afford NMR-pure product in 0.92 g (82.9%) yield.1H NMR (CDCl3, 500 MHz) δppm: 7.83 (s, 2H), 7.48 (d, J=8.5 Hz, 4H), 7.22 (d, J=16.5 Hz, 2H, ═CH), 7.01 (d, J=16.0 Hz, 2H, ═CH), 6.91 (d, J=9.0 Hz, 4H), 4.0 (t, J=6.5 Hz, 4H, CH2), 1.80 (m, 4H, CH2), 1.52 (m, 4H, CH2), 0.99 (t, J=7.2 Hz, 6H, CH3)—C NMR (CDCl3, 125.7 MHz) δppm: 159.5, 137.2, 131.6, 129.9, 129.2, 128.2, 123.4, 122.8, 114.7, 67.7, 31.3, 19.2, 13.9.

出典