5-Chloro-1-ethyl-3-vinyl-1H-pyrazole synthesis
- Product Name:5-Chloro-1-ethyl-3-vinyl-1H-pyrazole
- CAS Number:1278588-27-4
- Molecular formula:C7H9ClN2
- Molecular Weight:156.61
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Yield:1278588-27-4 5.72 g
Reaction Conditions:
Stage #1: 1,1-Dichloroethylene;2-Bromopropionyl chloridewith aluminum (III) chloride in dichloromethane at -5 - 20; for 9 h;
Stage #2: with triethylamine in diethyl ether at -5 - 20; for 0.5 h;
Stage #3: ethylhydrazineFurther stages;
Steps:
4.4. General procedure for the synthesis of 3-alkenyl-5-chloropyrazoles (5a-h)
General procedure: A solution of 3-haloalkylpyrazole 4a-d, 4k (50 mmol) or the mixtures of compounds 4a and 4e; 4b and 4f; 4c and 4g (obtained from 100 mmol of 2-bromopropanoyl chloride 1c, Scheme 2) or the mixture of compounds 4h and 5e; 4i, 5f and 6a; 4j, 5g and 6b (obtained from 50 mmol of 3d, Scheme 3) in DMF (20 mL) was exposed under MW irradiation (800 W) for 10-30 min. Then the reaction mixture was diluted with water (200 mL) and extracted with diethyl ether (3×50 mL). The extract was dried over MgSO4 and filtered off. Diethyl ether was evaporated and a target 3-alkenylpyrazole was distilled in vacuum or recrystallized.
References:
Levkovskaya, Galina G.;Kobelevskaya, Valentina A.;Rudyakova, Elena V.;Ha, Khanh Q.;Samultsev, Dmitrii O.;Rozentsveig, Igor B. [Tetrahedron,2011,vol. 67,# 10,p. 1844 - 1851] Location in patent:experimental part
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