Acetic Acid → Diethyl 3-ethyl-5-oxo-2,2-pyrrolidinedicarboxylate

HRID 640071노트

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HRID 640071 반응식
[Na].[C:2]([NH:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3].C(O[C:20](=O)/[CH:21]=[CH:22]/CC)C.C(O)(=O)C>C(O)C>[CH2:10]([O:9][C:7]([C:6]1([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:20]([CH2:21][CH3:22])[CH2:3][C:2](=[O:4])[NH:5]1)=[O:8])[CH3:11]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 14041Acetamidomalonic acid diethyl esterHCID 5360545SodiumHCID 5367761Ethyl trans-2-pentenoate

생성물 1

HCID 255944Diethyl 3-ethyl-5-oxo-2,2-pyrrolidinedicarboxylate수율 87.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To 150 mg of sodium dissolved in 150 mL of absolute ethanol was added diethyl acetamidomalonate (5.3 g, 25 mmol) and ethyl-(2E)-pent-2-enoate (3.5 g, 27.3 mmol). The reaction mixture was then refluxed for 20 h. After this period of time, 2 mL of glacial acetic acid was added, volatiles were removed under pressure with the aid of a water aspirator and heating bath. On cooling the residue solidified. The residue was dissolved in 50 mL of toluene and to this was added 20 mL of petroleum ether. The product precipitated when the mixture was cooled. The crystals were collected and washed with water and further dried in vacuo to obtain a white solid (5.6 g, 79.77%). Mass Spectrum (+ESI): 258 (M+H)+.

후처리

  1. temperatureThe reaction mixture was then refluxed for 20 h
  2. customvolatiles were removed under pressure with the aid of a water aspirator
  3. temperatureheating bath
  4. temperatureOn cooling the residue solidified
  5. dissolutionThe residue was dissolved in 50 mL of toluene
  6. additionto this was added 20 mL of petroleum ether
  7. customThe product precipitated when the mixture
  8. temperaturewas cooled
  9. customThe crystals were collected
  10. washwashed with water
  11. customfurther dried in vacuo

출처 및 근거

ORD 기록
ord-45ae26d02dc747afab8236f1d1b5ab4a
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691884B2

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