反応 #1256719

反応方程式

11

4-(4-iodo-2,6-dimethyl-phenyl)-3,5-dimethyl-pyridine

18

2-(4-vinyl-phenyl)-malononitrile

PPh3

→

title compound

収率 55.4%

2-(4-{2-[4-(3,5-dimethyl-pyridin-4-yl)-3,5-dimethyl-phenyl]-vinyl}-phenyl)-malononitrile

収率 55.4%

反応条件

後処理

1. 1
   その他evacuated
2. 2
   workup.ADDITIONNext, dry Et3N (5 mL) and dry DMF (10 mL) were added under an N2 flow
3. 3
   その他The Schlenk tube was sealed
4. 4
   その他the mixture was degassed by 3 freeze-thaw cycles
5. 5
   温度The reaction mixture was next cooled to room temperature
6. 6
   workup.ADDITIONpoured into water
7. 7
   抽出extracted with CH2Cl2 (3×50 mL)
8. 8
   乾燥The organic layer was dried over Na2SO4
9. 9
   ろ過filtered
10. 10
    濃縮concentrated in vacuo
11. 11
    その他The crude product was then purified by flash chromatography on silica gel
12. 12
    洗浄eluting with 1:1 hexane

実験手順

A flame-dried sealable Schlenk tube was charged with 11 (3.37 g, 10.0 mmol), 18 (2.52 g, 15.0 mmol), Pd(OAc)2 (224 mg, 1.00 mmol), and PPh3 (262 mg, 1.00 mmol), evacuated, and then backfilled with N2. Next, dry Et3N (5 mL) and dry DMF (10 mL) were added under an N2 flow. The Schlenk tube was sealed, and the mixture was degassed by 3 freeze-thaw cycles and backfilled with N2. The mixture was then covered with aluminum foil and stirred at 100° C. for 2 days. The reaction mixture was next cooled to room temperature, poured into water, neutralized with dilute HCl to pH=7, and extracted with CH2Cl2 (3×50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was then purified by flash chromatography on silica gel, eluting with 1:1 hexane: ethyl acetate to give 2.09 g (55.4%) of the title compound as red solid: mp 58-60° C.; 1H NMR (400 MHz, CDCl3): δ 8.405 (s, 2H), 7.640 (d, 2H, J=8.0 Hz), 7.506 (d, 2H, J=8.0 Hz), 7.337 (s, 2H), 7.160 (s, 2H), 1.936 (s, 6H), 1.929 (s, 6H); 13C NMR (100 MHz, CDCl3): δ 148.657, 148.093, 139.804, 137.383, 135.973, 135.218, 130.978, 127.911, 127.757, 126.774, 126.410, 124.863, 111.915, 28.096, 19.988, 16.749; MS (ESI): m/z 378.5 [M++H,100];MS (high resolution, EI): m/z 377.1878 [M+]; calcd, 377.1892; Anal. Calcd. for C26H23N3·1/2 H2O: C, 80.80; H, 6.26; N, 10.87. Found; C, 80.22; H, 6.32; N, 10.28.

出典