Reacción #1857591

Ecuación de reacción

4-(chloromethyl)-3,5-dimethylisoxazole

4-nitro-1H-pyrazole

t-BuOK

H2O

→

3,5-dimethyl-4-((4-nitro-1H-pyrazol-1-yl)methyl)isoxazole

Rendimiento 78.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas removed
2. 2
   TemperaturaThe reaction was refluxed for 16 hours
3. 3
   Otrothe precipitate formed
4. 4
   Filtraciónwas collected by filtration
5. 5
   LavadoThe precipitate was washed with additional H2O
6. 6
   Otrothen dried under high vacuum

Procedimiento

To 4-nitro-1H-pyrazole (Example 4-1d) (3.8 g, 34 mmol) in DMF (80 mL) cooled to 0° C., via an ice/water bath, was added t-BuOK (4.2 g, 38 mmol). After addition of the base the ice bath was removed and the mixture was stirred for 30 minutes followed by the addition of 4-(chloromethyl)-3,5-dimethylisoxazole (5 g, 34 mmol). The reaction was refluxed for 16 hours then cooled to ambient temperature. H2O was added to the reaction mixture and the precipitate formed was collected by filtration. The precipitate was washed with additional H2O then dried under high vacuum to afford 3,5-dimethyl-4-((4-nitro-1H-pyrazol-1-yl)methyl)isoxazole (5.8 g, 78%) as a light yellow solid. 1H NMR (CDCl3, 400 MHz): δ 2.23 (s, 3H), 2.46 (s, 3H), 5.08 (s, 2H), 8.02 (s, 1H), 8.08 (s, 1H).

Fuente