(E)-3-hydroxy-2-phenylprop-2-enenitrile

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-hydroxy-2-phenylacrylonitrile (3.4 mmol) in EtOH (6.8 mL) is added AcOH (0.66 mL) and 2-hydrazinopyridine (6.8 mmol) at room temperature. After stirred at 80° C. for 5 h, the reaction mixture is cooling and concentrated in vacuo. The residue is diluted with H2O and extracted with AcOEt. The organic extracts are washed with brine, dried over Na2SO4 and concentrated in vacuo. The resulting residue is triturated with ether to give the title compound; 1H NMR (CDCl3) δ 6.27 (br, 2H), 7.11-7.14 (m, 1H), 7.21-7.25 (m, 1H), 7.40-7.48 (m, 4H), 7.65 (s, 1H), 7.79-7.84 (m, 1H), 8.02 (d, 1H), 8.35-8.37 (m, 1H). the reaction mixture is cooling concentrated in vacuo The residue is diluted with H2O extracted with AcOEt The organic extracts are washed with brine dried over Na2SO4 concentrated in vacuo The resulting residue is triturated with ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Hydroxy-2-phenylacrylonitrile (12.3 g, 84.7 mmol) was dissolved in dry THF (100 ml) in a reaction vessel, and then NaH (4.1 g, 169.4 mmol) was slowly added thereto. The mixture was stirred at room temperature for 2 hr. Thereafter, dimethyl sulfate (13.7 ml, 144.0 mmol) was added, followed by stirring at 40° C. for 12 hr. After completion of the reaction, the reaction mixture was washed with distilled water and concentrated under reduced pressure. The concentrate was diluted with EtOAc and extracted with EtOAc together with distilled water. The organic layer was dried over anhydrous MgSO4 and filtered. The filtrate was concentrated under reduced pressure to give 17.9 g (112.5 mmol, quant.) of the title compound. by stirring at 40° C. for 12 hr After completion of the reaction the reaction mixture was washed with distilled water concentrated under reduced pressure The concentrate was diluted with EtOAc extracted with EtOAc together with distilled water The organic layer was dried over anhydrous MgSO4 filtered The filtrate was concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenylacetonitrile (10 g, 85.4 mmol) and methyl formate (67 ml) were dissolved in TIIF (250 ml) in a reaction vessel, and then NaH (2.6 g, 106.7 mmol) was added thereto at 0° C. The solution was stirred at room temperature for 12 hr. After completion of the reaction, the reaction mixture was washed with distilled water and acidified with 1 N HCl to adjust the pH to 5 or less. Thereafter, the resulting solution was extracted with dichloromethane. The organic layer was dried over anhydrous Na2SO4, followed by filtration. The filtrate was concentrated under reduced pressure to give 12.3 g (84.7 mmol, quant.) of the title compound. at 0° C After completion of the reaction the reaction mixture was washed with distilled water Thereafter, the resulting solution was extracted with dichloromethane The organic layer was dried over anhydrous Na2SO4 followed by filtration The filtrate was concentrated under reduced pressure

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-hydroxy-2-phenylacrylonitrile (3.4 mmol) in EtOH (6.8 mL) is added AcOH (0.66 mL) and 2-hydrazinopyridine (6.8 mmol) at room temperature. After stirred at 80° C. for 5 h, the reaction mixture is cooling and concentrated in vacuo. The residue is diluted with H2O and extracted with AcOEt. The organic extracts are washed with brine, dried over Na2SO4 and concentrated in vacuo. The resulting residue is triturated with ether to give the title compound; 1H NMR (CDCl3) δ 6.27 (br, 2H), 7.11-7.14 (m, 1H), 7.21-7.25 (m, 1H), 7.40-7.48 (m, 4H), 7.65 (s, 1H), 7.79-7.84 (m, 1H), 8.02 (d, 1H), 8.35-8.37 (m, 1H). the reaction mixture is cooling concentrated in vacuo The residue is diluted with H2O extracted with AcOEt The organic extracts are washed with brine dried over Na2SO4 concentrated in vacuo The resulting residue is triturated with ether