Acetic Acid → Diethyl 3-ethyl-1,3-dihydro-2H-pyrrole-2,2-dicarboxylate

HRID 1439706

Reaktionsgleichung

Reaktionsgleichung von HRID 1439706
C(O[C:9]([NH:11][CH:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=O)C1C=CC=CC=1.[Na].[CH:24](=O)[CH:25]=[CH:26][CH2:27]C.C(O)(=O)C>C(O)C.[Pd]>[CH2:25]([CH:26]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])([C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:11][CH:9]=[CH:27]1)[CH3:24]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 129932-PentenalHCID 259787Diethyl 2-(benzyloxycarbonylamino)malonateHCID 5360545Sodium

Produkt 1

HCID 21866300Diethyl 3-ethyl-1,3-dihydro-2H-pyrrole-2,2-dicarboxylateAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel4×

Versuchsvorschrift

Diethyl benzyloxycarbonylaminomalonate (11.5 g, 38 mM) was dissolved in dry ethanol (50 ml) and added to a solution of sodium (150 mg) in dry ethanol (10 ml). Pent-2-enal (3.2 g 38 mM) in ethanol (10 ml) was added dropwise to the stirred mixture and the solution stirred for 1 hr. A solution of acetic acid (0.29 ml) in ethanol (1 ml) was then added and the solution hydrogenated for 2 hrs at atmospheric pressure using palladium on carbon (5%) as catalyst. The catalyst was removed by filtration and the filtrate evaporated. The residue was dissolved in chloroform and the solution washed with brine containing a little sodium bicarbonate, dried (Na2SO4) and evaporated. Distillation of the residue at 15 mm Hg gave 4-ethyl-5,5-dicarboethoxy-2-pyrroline (5.65 g) as a colourless oil b.p. 115°-120° (15 mm Hg) I.R. 1715, 1610 cm-1.

Aufarbeitung

  1. waitthe solution hydrogenated for 2 hrs at atmospheric pressure
  2. customThe catalyst was removed by filtration
  3. customthe filtrate evaporated
  4. dissolutionThe residue was dissolved in chloroform
  5. washthe solution washed with brine containing a little sodium bicarbonate
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. distillationDistillation of the residue at 15 mm Hg

Quellen und Nachweise

ORD-Eintrag
ord-164814b4299a4fe7828b0c9496c9c3ae
Quelldatensatz
uspto-grants-1977_11
Patentnummer
US04060603

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