반응 #70768

반응 방정식

ethyl 2,4-dioxopentanoate

triethyl orthoformate

ammonium chloride

→

ethyl 4-ethoxy-2-oxopent-3-enoate

수율 79.0%

용매

ethanol

반응 조건

후처리

1. 1
   농축) The reaction was concentrated under vacuum
2. 2
   여과filtered
3. 3
   기타to remove insolubles
4. 4
   세척rinsed with Et2O
5. 5
   농축concentrated under vacuum
6. 6
   기타The product was obtained by short path distillation under vacuum (bp 70 to 77° C. at 0.09 mmHg)

실험 절차

To a stirred solution of ethyl 2,4-dioxopentanoate (36.5 g, 231 mmol) and triethyl orthoformate (41 mL, 246 mmol) in ethanol (60 mL) was added ammonium chloride (3.7 g, 69 mmol). The suspension was stirred at RT overnight. LCMS showed that the reaction was mostly complete. (Hydrolyzes on LCMS to some degree?) The reaction was concentrated under vacuum. The remaining oil was taken up in Et2O (300 mL), filtered to remove insolubles, rinsed with Et2O, and concentrated under vacuum. The product was obtained by short path distillation under vacuum (bp 70 to 77° C. at 0.09 mmHg) to give the product ethyl 4-ethoxy-2-oxopent-3-enoate (36.5 g, 47.3 mmol, 79% yield) as a light yellow oil.

출처