反応 #1256718

反応方程式

1-iodo-4-vinyl-benzene

HCl

NaH

malononitrile

→

title compound

収率 71.8%

2-(4-vinyl-phenyl)-malononitrile

収率 71.8%

溶媒

THF

1,2-dimethoxyethane

1,2-dimethoxyethane

反応条件

後処理

1. 1
   workup.STIRRINGthe reaction mixture stirred at 85° C. for 2 h
2. 2
   温度After cooling to room temperature
3. 3
   workup.ADDITIONthe reaction mixture was poured into ice
4. 4
   抽出extracted with CH2Cl2 (100 mL)
5. 5
   その他The organic layer was separated
6. 6
   乾燥dried over anhydrous Na2SO4
7. 7
   濃縮concentrated in vacuo
8. 8
   その他The crude product was then purified by flash chromatography on silica gel eluting with 1:1 hexane

実験手順

To an ice-cooled suspension of NaH (0.792 g, 33.0 mmol) in anhydrous 1,2-dimethoxyethane (20 mL) was added dropwise via syringe a solution of malononitrile (0.99 g, 15 mmol) in anhydrous 1,2-dimethoxyethane (5 mL) under N2. The mixture was stirred for 1 h at room temperature under N2. Next, 1-iodo-4-vinyl-benzene (1.15 g, 5.00 mmol), dry THF (15 mL), and tetrakis(triphenyphophine)palladium(0) (0.58g, 0.50 mmol) were added to the resulting pink suspension under an N2 flow, and the reaction mixture stirred at 85° C. for 2 h. After cooling to room temperature, the reaction mixture was poured into ice, neutralized with 10% HCl, and extracted with CH2Cl2 (100 mL). The organic layer was separated, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was then purified by flash chromatography on silica gel eluting with 1:1 hexane: CH2Cl2, to give 0.603 g (71.8%) of the title compound as pale yellow solid: mp 40-42° C. ° C; 1H NMR (400 MHz, CDCl3): δ 7.526 (d, 2H, J=7.6 Hz), 7.462 (d, 2H, J=7.6 Hz), 6.738 (d×d, 1H, J1=17.6 Hz, J2=10.8 Hz), 5.846 (d, 1H, J=17.6 Hz), 5.398 (d, 1H, J=10.8 Hz), 5.075 (s, 1H); 13C NMR (100 MHz, CDCl3): δ 139.840, 135.372, 127.766, 127.556, 125.245, 116.619, 111.897, 28.050; Anal. Calcd. for C11H8N2: C, 78.55; H, 4.79; N, 16.66. Found; C, 78.76; H, 4.75; N, 16.02.

出典