반응 #1857591

반응 방정식

4-(chloromethyl)-3,5-dimethylisoxazole

4-nitro-1H-pyrazole

t-BuOK

H2O

→

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

수율 78.0%

용매

DMF

반응 조건

후처리

1. 1
   기타was removed
2. 2
   온도The reaction was refluxed for 16 hours
3. 3
   기타the precipitate formed
4. 4
   여과was collected by filtration
5. 5
   세척The precipitate was washed with additional H2O
6. 6
   기타then dried under high vacuum

실험 절차

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).

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