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Volume 2005
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10.3390/M395
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Short Note

(Z)-2-Methyl-3-(1-phenyl-ethylamino)-but-2-enoic acid ethyl ester

by
Mercedes Pérez-Bonilla
,
Juan M. Castro
,
Pablo J. Linares-Palomino
,
Joaquín Altarejos
*,
Manuel Nogueras
,
Adolfo Sánchez
and
Sofía Salido
Departamento de Química Inorgánica y Orgánica, Facultad de Ciencias Experimentales, Universidad de Jaén, 23071 Jaén, Spain
*
Author to whom correspondence should be addressed.
Molbank 2005, 2005(1), M395; https://doi.org/10.3390/M395
Submission received: 16 February 2004 / Accepted: 7 July 2004 / Published: 1 July 2005
Versions Notes

Molbank 2005 m395 i001
p-Toluenesulfonic acid (48 mg, 0.25 mmol) was added to a stirred mixture of ethyl 2-methyl-acetoacetate (1) (346 mg, 2.40 mmol) and a-methylbenzylamine (2) (358 mg, 2.95 mmol) in toluene (13 mL) [1]. Then a Dean-Stark trap device was fit and the reaction refluxed overnight. The mixture was allowed to reach room temperature and percolated over a silica gel pad and the solvent evaporated under reduced pressure to yield the title compound 3 (540 mg, 2.32 mmol, 96%).
IR (neat, cm-1): 3250 (N-H), 3062, 3027, 780, 702 (Ph), 1646, 1250, 1121 (COOEt), 1598 (C=C–N).
1H NMR (300 MHz, CDCl3): δ= 1.30 (3H, t, J=7.1 Hz, CH3CH2O); 1.50 (3H, d, J=6.9 Hz, H-2’); 1.75* (3H, s, Me-2); 1.78* (3H, s, H-4); 4.16 (2H, dq, J=7.1, 1.0 Hz, CH3CH2O); 4.64 (1H, quint, J=6.9 Hz, H-1’); 7.18–7.35 (5H, m, Ph); 9.66 (1H, br d, J=6.9 Hz, NH).
*These signals may be interchanged.
13C NMR (75 MHz, CDCl3): δ= 171.10 (C-1); 87.70 (C-2); 159.00 (C-3); 15.75 (C-4); 12.54 (Me-2); 14.63 (CH3CH2O); 58.73 (CH3CH2O); 53.17 (C-1’); 25.17 (C-2’); 145.75 (C-3’); 125.44 (C-4’, C-8’); 128.65 (C-5’, C-7’); 126.80 (C-6’).
EI-MS (70 eV, m/z): 248 (M++H, 7%); 247 (M+, 14); 232 (M+–Me, 2); 218 (M+–Et, 0.7); 202 (M+–OEt, 3); 186 (4); 174 (M+–COOEt, 5); 145 (15); 105 (C8H9+, 100); 79 (10); 77 (10); 42 (13).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgement

We wish to thank the Ministerio de Ciencia y Tecnología for financial support (R+D Project PPQ2000-1665) and the Ministerio de Educación, Cultura y Deporte for a fellowship to J. M. Castro.

References

  1. Nour, M.; Tan, K.; Jankowski, R.; Cavé, C. Easy access to optically active Hagemann’s esters. Tetrahedron: Asymmetry 2001, 12, 765–769. [Google Scholar] [CrossRef]

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MDPI and ACS Style

Pérez-Bonilla, M.; Castro, J.M.; Linares-Palomino, P.J.; Altarejos, J.; Nogueras, M.; Sánchez, A.; Salido, S. (Z)-2-Methyl-3-(1-phenyl-ethylamino)-but-2-enoic acid ethyl ester. Molbank 2005, 2005, M395. https://doi.org/10.3390/M395

AMA Style

Pérez-Bonilla M, Castro JM, Linares-Palomino PJ, Altarejos J, Nogueras M, Sánchez A, Salido S. (Z)-2-Methyl-3-(1-phenyl-ethylamino)-but-2-enoic acid ethyl ester. Molbank. 2005; 2005(1):M395. https://doi.org/10.3390/M395

Chicago/Turabian Style

Pérez-Bonilla, Mercedes, Juan M. Castro, Pablo J. Linares-Palomino, Joaquín Altarejos, Manuel Nogueras, Adolfo Sánchez, and Sofía Salido. 2005. "(Z)-2-Methyl-3-(1-phenyl-ethylamino)-but-2-enoic acid ethyl ester" Molbank 2005, no. 1: M395. https://doi.org/10.3390/M395

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