Next Article in Journal
Synthesis of Ethyl (4-benzyl-3-methyl-6-oxopyridazin-1(6H)-yl)acetate
Previous Article in Journal
1-(2-ethoxy-2-oxoethyl)-5-methyl-1H-pyrazole-3-ethyl carboxylate
 
 
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Short Note

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

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), M528; https://doi.org/10.3390/M528
Submission received: 20 April 2006 / Accepted: 10 May 2006 / Published: 31 May 2007
Molbank 2007 m528 i001
A mixture of 1 (2g; 14.3mmol) and potassium tert-butoxide (1.68g; 15mmol) in 80ml of anhydrous diethyl ether was refluxed for 75min. After cooling at 0°C, a solution of ethylbromoacetate (3.27g; 19.6mmol) in 15ml of anhydrous diethyl ether was gradually added. The reaction mixture was stirred for one night at room temperature then filtered and the solvent was eliminated under reduced pressure. The obtained residue was purified on alumina using hexane as eluant to afford a 30% yield of the new compound 2 (white solid) (0.97g; 4.3mmol). The second waited isomer has not been isolated. The product 2 was identified on the basis of its spectroscopic data. The coupling constant of the 1H NMR between the proton in position 4 and the methyl group of pyrazol ring 4J(Me-H4) was 0.71Hz. This coupling is characteristic of a 5-methyl group [1,2,3].
Melting point: 54-56°C
1H-NMR (CDCl3, 300 MHz): δ= 6.41 (s, 1H, Pz-H); 4.80 (s, 2H, N-CH2-); 4.15 (q, 2H, -CH2-CH3 , J=7.13 Hz); 3.78 (s, 3H, -O-CH3); 2.20 (s, 3H, -CH3);1.23 (t, 3H, CH2-CH3 , J=7.13 Hz).
13C-NMR (CDCl3, 75 MHz): δ= 168.04; 163.45; 144.35; 142.62; 111.61; 64.95; 54.91; 54.22; 17.00; 13.49.
IR (KBr, cm-1): 1715 and 1735 (C=O).
Elemental analysis calculated for C10H14N2O4: C 53.09, H 6.24, N 12.38. Found: C 53.42, H 6.22, N 12.07.
Mass Spectrometry (ESI): m/z =227(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.

Share and Cite

MDPI and ACS Style

Attayibat, A.; Radi, S.; Lekchiri, Y.; Ramdani, A.; Bacquet, M. 1-(2-ethoxy-2-oxoethyl)-5-methyl-1H-pyrazole-3-methyl carboxylate. Molbank 2007, 2007, M528. https://doi.org/10.3390/M528

AMA Style

Attayibat A, Radi S, Lekchiri Y, Ramdani A, Bacquet M. 1-(2-ethoxy-2-oxoethyl)-5-methyl-1H-pyrazole-3-methyl carboxylate. Molbank. 2007; 2007(2):M528. https://doi.org/10.3390/M528

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-methyl carboxylate" Molbank 2007, no. 2: M528. https://doi.org/10.3390/M528

Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.

Article Metrics

Back to TopTop