Diethyl acetonedicarboxylate → HCID 54034256, Verbindung

HRID 325420

Reaktionsgleichung

Reaktionsgleichung von HRID 325420
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10](=O)[C:11](=[N:19]O)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:5]=[CH:6][CH:7]=1.[CH3:22][CH2:23][O:24][C:25]([CH2:27][C:28]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=O)=[O:26].C([O-])(=O)C.[Na+]>[Zn].C(O)(=O)C>[C:15]([O:14][C:12]([C:11]1[NH:19][C:28]([CH2:27][C:25]([O:24][CH2:23][CH3:22])=[O:26])=[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:10]=1[CH2:9][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Komponenten

6

Edukt 3

HCID 66045Diethyl acetonedicarboxylateHCID 517045Sodium AcetateHCID 178451312HCID 178451312, Verbindung

Produkt 1

HCID 54034256HCID 54034256, VerbindungAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Crude t-butyl 5-(m-chlorophenyl)-2-hydroximino-3-oxopentanoate (43 g., 0.15 mol) and diethyl acetonedicarboxylate (28 ml, 30.3 g, 0.15 mol) are placed in a 1 liter round bottom flask and 250 ml of glacial acetic acid added. With stirring, 25 g (0.30 mol) anhydrous sodium acetate is added followed by 26 g Zn dust (94% fine, 0.364 mol) in a portionwise manner so that the exotherm does not bring the reaction to reflux. When addition is complete, the reaction is heated on a steam bath for one hour. The hot solution is then decanted from the residual zinc into 3 liters of ice water, and the resulting mixture is stirred vigorously until the oil solidifies. The mixture is then allowed to stand for 1.5 hours, and the solid is filtered. The solid is washed with water, dried in vacuo and recrystallized to give 21.5 g (31%) of ethyl 5-(t-butoxycarbonyl)-4-[2-(m-chlorophenyl)ethyl]-3-ethoxycarbonylpyrrole-2-acetate, M.P. 131°- 132°.

Aufarbeitung

  1. customthe reaction
  2. temperatureto reflux
  3. additionWhen addition
  4. temperaturethe reaction is heated on a steam bath for one hour
  5. customThe hot solution is then decanted from the residual zinc into 3 liters of ice water
  6. stirringthe resulting mixture is stirred vigorously until the oil
  7. filtrationthe solid is filtered
  8. washThe solid is washed with water
  9. customdried in vacuo
  10. customrecrystallized

Quellen und Nachweise

ORD-Eintrag
ord-505488170c2b4d528249f20b4bfb6f2c
Quelldatensatz
uspto-grants-1984_04
Patentnummer
US04440779

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