(E)-tert-butyl 3-(4-cyanophenyl)acrylate

(E)-tert-butyl 3-(4-cyanophenyl)acrylate

A flame-dried three-neck round-bottom flask equipped with a magnetic stirring bar, a thermometer, an addition funnel and a nitrogen inlet was charged with NaH (3.96 g, 94.7 mmol) and anhydrous THF (120 mL). Tertbutyldiethylphosphono acetate (23.2 mL, 94.7 mmol) dissolved in anhydrous THF (20 mL) was added dropwise via the addition funnel over a period of 30 min. After the completion of addition, the reaction mixture was stirred at rt for another 30 min. A solution of 4- cyanobenzaldehyde (1 1 .3 g, 86.1 mmol) dissolved in anhydrous THF (20 mL) was added to the reaction mixture dropwise via the addition funnel over a period of 30 min. After the end of the addition, the reaction mixture was stirred at rt for 1 h, then diluted with MTBE (200 mL) and sat. NH₄CI (150 mL). The organic layer was separated, washed with 25 mL of H₂0 and 25 mL of sat. NH₄CI, dried over MgS0₄, filtered and evaporated to dryness to give 20.0 g Intermediate G as a solid (100%). 

¹H NMR (400 MHz, CDCI₃) δ ppm 1 .56 (s, 9H) 6.47 (d, J=16 Hz, 1 H) 7.58 (d, J=16 Hz, 1 H) 7.61 (d, J=8 Hz, 2H) 7.68 (d, J=8 Hz, 2H)

http://www.google.com/patents/EP2536701A1?cl=en









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