Ethyl Acetoacetate → 3-Chloro-but-2-enoic acid ethyl ester

HRID 18964

반응식

HRID 18964 반응식
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=O.P(Cl)(Cl)(Cl)(Cl)[Cl:11]>O>[CH2:8]([O:7][C:1](=[O:6])[CH:2]=[C:3]([Cl:11])[CH3:5])[CH3:9]

참가 물질

4

반응물 2

HCID 8868Ethyl AcetoacetateHCID 24819Phosphorus pentachloride

생성물 1

HCID 2828353-Chloro-but-2-enoic acid ethyl ester수율 83%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
25 °C

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.

후처리

  1. additionAfter addition
  2. additionwas added in small portions
  3. customtransferred to a separatory funnel
  4. customthe layers separated
  5. washby washing the aqueous layer with petroleum ether (2×50 mL)
  6. washThe combined petroleum ether extracts were washed with a 20% potassium carbonate solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe combined organic layers were concentrated
  9. customto give a yellow oil
  10. distillationDistillation of the residue

출처 및 근거

ORD 기록
ord-e6036ef11aa9408e8fa664960532b4d3
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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