3-(3-oxoprop-1-enyl)benzonitrile

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

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 suspension of active manganese dioxide (20 g) in a solution of 3-cyanocinnamyl alcohol (Example 10(d), 4.0 g) in dichloromethane (100 ml) was stirred at room temperature for 16 hours. The mixture was filtered and the filtrate was evaporated to give the title product as a white solid, m.p. 100° C. The mixture was filtered the filtrate was evaporated

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

Procedure: A suspension of active manganese dioxide (20 g) in a solution of 3-cyanocinnamyl alcohol (Example 10(d), 4.0 g) in dichloromethane (100 ml) was stirred at room temperature for 16 hours. The mixture was filtered and the filtrate was evaporated to give the title product as a white solid, m.p. 100° C. The mixture was filtered the filtrate was evaporated

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

Procedure: A suspension of active manganese dioxide (20 g) in a solution of 3-cyanocinnamyl alcohol (Example 10(d), 4.0 g) in dichloromethane (100 ml) was stirred at room temperature for 16 hours. The mixture was filtered and the filtrate was evaporated to give the title product as a white solid, m.p. 100° C. The mixture was filtered the filtrate was evaporated

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

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

Procedure: The compound is prepared according to the method described in Example 1A from 3-cyanocinnamaldehyde (2.54 mmol) and from thiosemicarbazide (2.54 mmol). Yield 46%. The compound is prepared

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-cyanobenzaldehyde (4.5 g) in toluene (200 ml) was added (triphenylphosphoranylidene)acetaldehyde (13.6 g), and the resulting mixture was stirred at 70° C. for 4 hours and then evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using dichloromethane as the eluent. The crude product obtained was recrystallized from a mixture of toluene and hexane to afford the title compound (3.09 g, yield: 57%) as pale yellowish needle crystals. evaporated in vacuo The residue obtained was purified by chromatography on a silica gel column The crude product obtained was recrystallized from a mixture of toluene and hexane

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

Procedure: A suspension of active manganese dioxide (20 g) in a solution of 3-cyanocinnamyl alcohol (Example 10(d), 4.0 g) in dichloromethane (100 ml) was stirred at room temperature for 16 hours. The mixture was filtered and the filtrate was evaporated to give the title product as a white solid, m.p. 100° C. The mixture was filtered the filtrate was evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 3-cyano-1-(2-formylethenyl)benzene (1 g) in 30 mL of MeOH were added CeCl3 (1.88 g) and the resulting solution was stirred for 30 minutes and cooled to 0° C. To the solution was then added NaBH4 (0.29 g). The resulting solution was stirred for 1 hour at 0° C. and concentrated. The residue was taken up in 100 mL of saturated aqueous NaHCO3 and extracted with ethyl acetate (3×). The organic layer was dried, concentrated and purified on silica gel column (ethyl acetate/hexane, 1:4) to give 0.73 g of 3-cyano-1-(3-hydroxyprop-2-en-1 yl)benzene. The resulting solution was stirred for 1 hour at 0° C. concentrated extracted with ethyl acetate (3×) The organic layer was dried concentrated purified on silica gel column (ethyl acetate/hexane, 1:4)

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

Procedure: A mixture of 3-cyanobenzaldehyde (2.0 g) and (triphenylphosphoranylidene) acetaldehyde (5.0 g) in 100 mL CH2Cl2 was stirred at reflux for 16 hours. The reaction was cooled, concentrated and purified on silica gel column (ethyl acetate/hexane=3/7) to afford 2.2 g of 3-cyano-1-(2-formylethenyl)benzene as a yellow oil. at reflux for 16 hours The reaction was cooled concentrated purified on silica gel column (ethyl acetate/hexane=3/7)