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[Practical Example]▶ Isoxazole Ring Construction Reaction Using Hydroxylamine Hydrochloride
TCI Practical Example에서는 TCI의 합성 담당 연구원이 직접 겪은 반응 사례를 분석 자료와 함께 소개하고 있습니다.
[20240318]
"Isoxazole ring construction reaction using hydroxylamine hydrochloride and 1,3-diphenyl-1,3-propanedione"
Used Chemicals
Procedure
Hydroxylamine hydrochloride (396 mg, 6.0 mmol, 1.2 eq.) was added to a solution of 1,3-diphenyl-1,3-propanedione (1.12 g, 5.0 mmol) in ethanol (20 mL) at room temperature. The mixture was refluxed for overnight. Then water (80 mL) was added to the reaction mixture and precipitate was filtered to give 3,5-diphenylisoxazole as a pale red solid (1.09 g, 99% yield).
Experimenter’s Comments
The reaction mixture was monitored by UPLC.
Analytical Data
3,5-Diphenylisoxazole
1H NMR (400 MHz, CDCl3); δ 7.87-7.83 (m, 4H), 7.50-7.46 (m, 6H), 6.82 (s, 1H).
Lead Reference
- Photocycloaddition of aromatic and aliphatic aldehydes to isoxazoles: Cycloaddition reactivity and stability studies
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