Réaction #1857591

Équation de réaction

4-(chloromethyl)-3,5-dimethylisoxazole

4-nitro-1H-pyrazole

t-BuOK

H2O

→

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

Rendement 78.0%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Autrewas removed
2. 2
   TempératureThe reaction was refluxed for 16 hours
3. 3
   Autrethe precipitate formed
4. 4
   Filtrationwas collected by filtration
5. 5
   LavageThe precipitate was washed with additional H2O
6. 6
   Autrethen dried under high vacuum

Mode opératoire

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).

Source