反应 #1857591

反应方程式

4-(chloromethyl)-3,5-dimethylisoxazole

4-nitro-1H-pyrazole

t-BuOK

H2O

→

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

收率 78.0%

溶剂

DMF

反应条件

后处理

1. 1
   其他was removed
2. 2
   温度The reaction was refluxed for 16 hours
3. 3
   其他the precipitate formed
4. 4
   过滤was collected by filtration
5. 5
   洗涤The precipitate was washed with additional H2O
6. 6
   其他then dried under high vacuum

实验过程

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).

来源