Reacción #1256718

Ecuación de reacción

1-iodo-4-vinyl-benzene

HCl

NaH

malononitrile

→

title compound

Rendimiento 71.8%

2-(4-vinyl-phenyl)-malononitrile

Rendimiento 71.8%

Disolventes

THF

1,2-dimethoxyethane

1,2-dimethoxyethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction mixture stirred at 85° C. for 2 h
2. 2
   TemperaturaAfter cooling to room temperature
3. 3
   workup.ADDITIONthe reaction mixture was poured into ice
4. 4
   Extracciónextracted with CH2Cl2 (100 mL)
5. 5
   OtroThe organic layer was separated
6. 6
   Secadodried over anhydrous Na2SO4
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   OtroThe crude product was then purified by flash chromatography on silica gel eluting with 1:1 hexane

Procedimiento

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.

Fuente