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Volume 2007
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Short Note

1-(2-ethoxy-2-oxoethyl)-5-methyl-1H-pyrazole-3-ethyl carboxylate

by
Ahmed Attayibat
1,*,
Smaail Radi
1,
Yahya Lekchiri
2,
Abdelkrim Ramdani
1 and
Maryse Bacquet
3
1
Laboratoire de Chimie Organique Physique, Département de Chimie, Université Mohamed 1er, BP 524, 60 000 Oujda, Morocco
2
Laboratoire de Biochimie, Département de Biologie, Faculté des Sciences, Université Mohamed 1er, BP 524, 60 000 Oujda, Morocco
3
Laboratoire de Chimie Macromoléculaire, Université des Sciences et Technologies de Lille, 59655 Villeneuve d’Ascq, France
*
Author to whom correspondence should be addressed.
Molbank 2007, 2007(2), M527; https://doi.org/10.3390/M527
Submission received: 20 April 2006 / Accepted: 10 May 2006 / Published: 31 May 2007
Versions Notes

Molbank 2007 m527 i001
A mixture of 1 (6g; 39mmol) and potassium tert-butoxide (4.62g; 41.3mmol) in 120ml of anhydrous diethyl ether was refluxed for 75min. After cooling at 0°C, a solution of ethylbromoacetate (8.46g; 50.6mmol) in 20ml of anhydrous diethyl ether was slowly added. The reaction mixture was stirred for one night at room temperature then filtered and the solvent was evaporated to dryness. The obtained residue was purified on alumina using hexane as eluant to give a 15% yield of the new compound 2 (yellow oil) (1.4g; 5.83mmol).
1H NMR spectrum of the compound 2 has a methyl group of pyrazol moiety at 2.33 ppm and a H4 proton at 6.80 ppm with a 4J(Me-H4) = 0.72 Hz. Theses couplings being characteristic of a 5-methyl group [1,2,3]. Thus,the 1H NMR spectrum is consistent with the structure 2.
1H-NMR (CDCl3, 300 MHz ): δ= 6.80 (s, 1H, Pz-H); 5.10 (s, 2H, N-CH2-); 4.50 (q, 2H, -CH2-CH3 , J=7Hz); 4.40 (q, 2H, -CH2-CH3 , J=7Hz); 2.33 (s, 3H, -CH3); 1.40 (t, 3H, CH2-CH3, J=7Hz); 1.28 (t, 3H, CH2-CH3, J=7Hz).
13C-NMR (CDCl3, 75 MHz ): δ= 167.03; 162.35; 143.30; 141.02; 108.69; 62.05; 60.93; 51.30; 14.39; 14.10; 11.08.
Elemental analysis calculated for C11H16N2O4: C 55.00, H 6.71, N 11.66. Found: C 55.43, H 6.81, N 11.77.
IR (KBr, cm-1): 1720 and 1740 (C=O).
Mass Spectrometry (ESI): m/z =241(M+1)

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References:

  1. Tarrago, G.; Ramdani, A.; Elguero, J.; Espada, M. J. Heterocycl. Chem. 1980, 17, 137.
  2. Gready, J.E.; Hatton, P.M.; Sternhell, S. J. Heterocycl. Chem. 1992, 29, 935.
  3. Kumar, D.; Singh, S.P.; Martinez, A.; Fruchier, A.; Elguero, J.; Martinez-Ripoll, M.; Carrio, J.S.; Virgili, A. Tetrahedron 1995, 51, 4891.

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MDPI and ACS Style

Attayibat, A.; Radi, S.; Lekchiri, Y.; Ramdani, A.; Bacquet, M. 1-(2-ethoxy-2-oxoethyl)-5-methyl-1H-pyrazole-3-ethyl carboxylate. Molbank 2007, 2007, M527. https://doi.org/10.3390/M527

AMA Style

Attayibat A, Radi S, Lekchiri Y, Ramdani A, Bacquet M. 1-(2-ethoxy-2-oxoethyl)-5-methyl-1H-pyrazole-3-ethyl carboxylate. Molbank. 2007; 2007(2):M527. https://doi.org/10.3390/M527

Chicago/Turabian Style

Attayibat, Ahmed, Smaail Radi, Yahya Lekchiri, Abdelkrim Ramdani, and Maryse Bacquet. 2007. "1-(2-ethoxy-2-oxoethyl)-5-methyl-1H-pyrazole-3-ethyl carboxylate" Molbank 2007, no. 2: M527. https://doi.org/10.3390/M527

APA Style

Attayibat, A., Radi, S., Lekchiri, Y., Ramdani, A., & Bacquet, M. (2007). 1-(2-ethoxy-2-oxoethyl)-5-methyl-1H-pyrazole-3-ethyl carboxylate. Molbank, 2007(2), M527. https://doi.org/10.3390/M527

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