Diethyl formamidomalonate → 1-Formyl-5-hydroxy-4-[2-nitrophenyl]-pyrrolidine-2,2-dicarboxylic acid diethylester

HRID 1390831

Reaktionsgleichung

Reaktionsgleichung von HRID 1390831
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[CH2:13])[CH:11]=[O:12])([O-:3])=[O:2].[CH:14]([NH:16][CH:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:15].[O-]CC.[Na+]>C(O)C>[CH2:26]([O:25][C:23]([C:17]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13][CH:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH:11]([OH:12])[N:16]1[CH:14]=[O:15])=[O:24])[CH3:27]

Komponenten

5

Edukt 3

HCID 80617Diethyl formamidomalonateHCID 2723922Sodium ethoxideHCID 27770992-(2-Nitrophenyl)acrylaldehyde

Produkt 1

HCID 128784961-Formyl-5-hydroxy-4-[2-nitrophenyl]-pyrrolidine-2,2-dicarboxylic acid diethylester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel3×

Versuchsvorschrift

To a stirred, icebath-cooled mixture of 42.5 g. (0.24 mol) of acrolein of Example 1 and 50.4 g (0.25 mol) of diethyl formamidomalonate in 200 ml. of absolute ethanol was added, over 15 minutes, 4 ml. of a 1M solution of sodium ethoxide in ethanol. The mixture was stirred at 5° for 1 hour as the Michael adduct crystallized out. After the suspension had been stored for 4 hours at -20°, the product was collected by filtration washed with ethanol (-60°) and dried to yield 82.4 g (90%) of offwhite crystals, m.p. 109-111°. The analytical sample was prepared by recrystallization from ethanol: white crystals, m.p. 113-115°.

Aufarbeitung

  1. temperatureTo a stirred, icebath-cooled
  2. additionmixture of 42.5 g
  3. customcrystallized out
  4. waitAfter the suspension had been stored for 4 hours at -20°
  5. filtrationthe product was collected by filtration
  6. washwashed with ethanol (-60°)
  7. customdried
  8. customto yield 82.4 g (90%) of offwhite crystals, m.p. 109-111°

Quellen und Nachweise

ORD-Eintrag
ord-1ceaaac4365f4789bb123b0007e30ab2
Quelldatensatz
uspto-grants-1979_02
Patentnummer
US04140697

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