Molbank 2005, M452

http://www.mdpi.net/molbank/

 

Synthesis of 6-carbomethoxy-3-Phenyl-5-(4-dimethylaminophenyl)-cyclohexenone

 

Gricela M. Lobo*, Jaime E. Charris

 

Laboratorio de S¨ªntesis Org¨¢nica, Facultad de Farmacia,

Universidad Central de Venezuela, Caracas 1051, Venezuela,

e-mail: [email protected], [email protected]

 

Received: 12 October 2005 / Accepted: 1 December 2005 / Published: 12 December 2005

 

Keywords:

 

A mixture of 4-dimethylaminochalcone 1 (0.25 g, 1.00 mmol), methyl acetoacetate (0.17 g, 1.5 mmol) in methanol (5.00 mL) and sodium metoxide (0.25 mg) was stirred at room temperature for 24 hour to give a yellow precipitate. Then it was filtered and washed with water. Recrystalized of the crude substance from methanol afforded pure cyclohexenone 2 (2.27 g, 97.00 %).

 

Melting point: 134-136 ºC.

 

IR (KBr, cm-1): 1740(CO); 1666 (CO).

 

1H-NMR (CDCl3, 270 MHz): d= 7.59 (d, 2H, J = 8.56 Hz), 7.33 (dd, 2H, J = 8.56, 8.56 Hz), 7.24 (dd, 2H, J = 8.50, 2.2 Hz) 6.58 (d, 1H J = 1.98 Hz), 6.60 (dd, 2H, J = 8.56, 8,56 Hz), 3.82 (dd, 1H, J = 5.4, 2.45 Hz), 3.58 (s, 3H, CO2CH3), 3.10 (dt, 1H, J = 12.5, 3.7, 1.98 Hz), 3.01 (d, 1H, J = 12.5 Hz), 2.98 (s, 6H, (CH3)2N).

13C NMR (CDCl3) (270 MHz) d (ppm): 190.0 (C=O), 174.8 (COO), 141.3, 128.6, 127.2, 126.8, 111.9 (aromatic carbons), 149.6, 120.3, 59.2, 52.5, 44,5, 39.2, 31.5.

 

MS (m/z, %): 351(M + 1, 10), 292 (351- CO2CH3,100).

 

Reference:

1. Rojas, Jos¨¦ N. Dom¨ªnguez, Jaime E. Charris, Gricela Lobo, Miguel Pay¨¢ and M. Luisa Ferr¨¢ndiz European Journal of Medicinal Chemistry, 2002, 37, 699-.

 

Sample Availability: Available from MDPI.

 

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