.beta.,.beta.-Diphenylacrylonitrile

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A mixture of 3,3-diphenylacrylonitrile (5.76 g, 28.1 mmol) and sodium hydroxide (11.2 g) in ethylene glycol (180 mL) and water (1 mL) were refluxed for 3 days. The reaction mixture was diluted with water (100 mL), acidified with 5N HCl to pH˜1, and extracted with ethyl acetate. The organic extract was washed with water, dried over sodium sulfate, and concentrated in vacuo. The crude material was purified by flash column chromatography ethyl acetate/hexanes to give 3,3-diphenylacrylic acid (5.1 g, 81%) as a white powder. were refluxed for 3 days extracted with ethyl acetate The organic extract was washed with water dried over sodium sulfate concentrated in vacuo The crude material was purified by flash column chromatography ethyl acetate/hexanes

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

Procedure: To a solution of benzophenone (9.1 g, 50 mmol) in acetonitrile (20 mL) was added potassium hydroxide (3.3 g, 50 mmol) in acetonitrile (25 mL). The solution was refluxed for 8 hours. The hot reaction mixture was poured into 100 g crushed ice and then extracted with dichloromethane. The organic extract was washed with water, dried over sodium sulfate, and concentrated in vacuo. The crude material was purified by flash column chromatography (diethyl ether/hexanes) to give 3,3-diphenylacrylonitrile (7.7 g, 73.3%) as an oil. The solution was refluxed for 8 hours The hot reaction mixture was poured into 100 g crushed ice extracted with dichloromethane The organic extract was washed with water dried over sodium sulfate concentrated in vacuo The crude material was purified by flash column chromatography (diethyl ether/hexanes)

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3,3-diphenylacrylonitrile (4.45 g, 21.7 mmol) in THF (75 mL) at 0° C. was added aluminum(III) chloride (3.27 g, 24.5 mmol) and lithium tetrahydroaluminate (1 M in THF) (0.910 g, 24.0 mmol) (24 mL). The reaction mixture was warmed to room temperatrue and stirred for 1 h, heated to 40° C. for 2 h, heated to 60° C. for 2 h, quenched with water (5 mL), adjusted to pH 12 with ammonium hydroxide, diluted with brine, and EtOAc, extracted with EtOAc (5×), combined organic extracts washed with brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 3% to 10% MeOH (2 M NH3) in DCM) gave 3,3-diphenyl-2-propenylamine. The reaction mixture was warmed to room temperatrue heated to 60° C. for 2 h quenched with water (5 mL) diluted with brine, and EtOAc extracted with EtOAc (5×) combined organic extracts washed with brine (1×) dried over MgSO4 filtered concentrated Purification by flash column chromatography on silica gel (eluted with 3% to 10% MeOH (2 M NH3) in DCM)

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

Procedure: To a suspension of sodium hydride (60% wt in mineral oil) (0.780 g, 32.5 mmol) in THF (100 mL) at room temperature was added diethyl cyanomethylphosphonate (4.50 g, 25.4 mmol) (4 mL). The mixture was stirred for 30 min and benzophenone (4.22 g, 23.2 mmol) was added. The reaction mixture was stirred at room temperature for 1d, and partially concentrated, diluted with Et2O, washed with water (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 5% to 20% EtOAc in hexanes) gave 3,3-diphenylacrylonitrile. partially concentrated diluted with Et2O washed with water (1×), brine (1×) dried over MgSO4 filtered concentrated Purification by flash column chromatography on silica gel (eluted with 5% to 20% EtOAc in hexanes)

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

Procedure: A mixture of 3,3-diphenylacrylonitrile (5.76 g, 28.1 mmol) and sodium hydroxide (11.2 g) in ethylene glycol (180 mL) and water (1 mL) were refluxed for 3 days. The reaction mixture was diluted with water (100 mL), acidified with 5N HCl to pH˜1, and extracted with ethyl acetate. The organic extract was washed with water, dried over sodium sulfate, and concentrated in vacuo. The crude material was purified by flash column chromatography ethyl acetate/hexanes to give 3,3-diphenylacrylic acid (5.1 g, 81%) as a white powder. were refluxed for 3 days extracted with ethyl acetate The organic extract was washed with water dried over sodium sulfate concentrated in vacuo The crude material was purified by flash column chromatography ethyl acetate/hexanes

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

Procedure: To a solution of benzophenone (9.1 g, 50 mmol) in acetonitrile (20 mL) was added potassium hydroxide (3.3 g, 50 mmol) in acetonitrile (25 mL). The solution was refluxed for 8 hours. The hot reaction mixture was poured into 100 g crushed ice and then extracted with dichloromethane. The organic extract was washed with water, dried over sodium sulfate, and concentrated in vacuo. The crude material was purified by flash column chromatography (diethyl ether/hexanes) to give 3,3-diphenylacrylonitrile (7.7 g, 73.3%) as an oil. The solution was refluxed for 8 hours The hot reaction mixture was poured into 100 g crushed ice extracted with dichloromethane The organic extract was washed with water dried over sodium sulfate concentrated in vacuo The crude material was purified by flash column chromatography (diethyl ether/hexanes)

Conditions: temp:0.00; pressure:0.00; stir: