1-Hydroxymethyl-3-ethoxy-5-methylpyrazole

Rachid Touzani*, Abdelkrim Ramdani*, Sghir El Kadiri* and Fabienne Gourand**

* Laboratory of Chemistry Organic-Physics, Departement of Chemistry, Faculty of Sciences, University of Mohammed The First, BP 524-60000-Oujda, Morocco (E-mail: [email protected], E-mail: [email protected])

**Laboratory of Chemistry Sciences, University of Caen, France

Received: 18 September 1999 / Accepted: 4 October1999 / Published: 23 November 1999

The product 2 was prepared by the addition of formalin (CH₂O) to 1 [1] according to the reported procedure [2]. The diazole 1 (6.16g, 0.04mol) was dissolved in ethanol (20ml) and formalin (5ml, 40%) was added and the mixture was heated to reflux for 1 h. The reaction was continued at room temperature for 12 h and the mixture was concentrated under reduced pressure. The unreacted formalin was removed by extraction in a ether/water mixture. The organic solution was concentrated in vacuum and the crude product was recrystallized from ether to yield 2 as a white solid (5.52g, 75%).

M.p. 70-72 °C.

IR (KBr, cm^-1): 3274, 1722, 1600, 1550, 1448, 1330, 1236, 1029, 780, 760, 750.

¹H NMR (CDCl₃): 6.50 (s, 1H, CH); 5.52 (s, 2H, CH₂OH); 4.35-4.25 (q, 2H, CH₂CH₃); 2.35 (s, 3H, CH₃); 1.35-1.27 (t, 3H, CH₂CH₃).

MS (m/z): 185; 168; 155; 140; 127; 110; 82; 53.

Acknowledgement: We gratefully acknowledge Abdelkrim Ramdani for his generous support.

References

1. Jones, R. G.; Hanret, M. J.; Lauglin, K. M. J. Org. Chem. 1954, 19, 1428.

2. Elguero, J. Heterocycles 1986, 24, 2233.

Sample availability: available from the authors and MDPI.

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