반응 #47242

반응 방정식

ethyl acetoacetate

phosphorus pentachloride

→

3-chloro-but-2-enoic acid ethyl ester

수율 83.0%

용매

water

—

petroleum ether

반응 조건

후처리

1. 1
   workup.ADDITIONAfter addition
2. 2
   workup.ADDITIONwas added in small portions
3. 3
   기타transferred to a separatory funnel
4. 4
   기타the layers separated
5. 5
   세척by washing the aqueous layer with petroleum ether (2×50 mL)
6. 6
   세척The combined petroleum ether extracts were washed with a 20% potassium carbonate solution
7. 7
   건조dried over magnesium sulfate
8. 8
   농축The combined organic layers were concentrated
9. 9
   기타to give a yellow oil
10. 10
    workup.DISTILLATIONDistillation of the residue

실험 절차

To a stirred mixture of ethyl acetoacetate (15.0 g, 0.12 mol) in petroleum ether (30 mL) under a nitrogen atmosphere was added phosphorus pentachloride (12.7 g, 0.06 mol) gradually. After addition was complete the mixture was stirred at 25° C. for 1 h. Upon completion of the reaction water (50 mL) was added in small portions, transferred to a separatory funnel and the layers separated, followed by washing the aqueous layer with petroleum ether (2×50 mL). The combined petroleum ether extracts were washed with a 20% potassium carbonate solution, followed by a saturated sodium chloride solution and dried over magnesium sulfate. The combined organic layers were concentrated to give a yellow oil. Distillation of the residue yielded 3-chloro-but-2-enoic acid ethyl ester (7.4 g 43%) as a clear oil: LR-ES-MS m/z calculated for C6H9ClO2 [M]+ 148, observed [M+H]+ 149.

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