Diethyl Malonate → Diethyl 2-(3-methyl-2-nitrobenzylidene)malonate

HRID 1435937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1435937
[CH3:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:13]([O:21][CH2:22][CH3:23])(=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)(O)[O-].[Na+]>C(OC(=O)C)(=O)C>[CH3:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:13]([O:21][CH2:22][CH3:23])=[O:20]

Komponenten

5

Edukt 3

HCID 7761Diethyl MalonateHCID 516892Sodium BicarbonateHCID 135735673-Methyl-2-nitrobenzaldehyde

Produkt 1

HCID 68898055Diethyl 2-(3-methyl-2-nitrobenzylidene)malonateAusbeute 90,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of this aldehyde (10.0 g, 60.6 mmol) in 20 mL of acetic anhydride was added diethyl malonate (9.7 g, 60.6 mmol) and sodium bicarbonate (7.6 g, 91 mmol). The reaction mixture was stirred at 100° C. for 24 h. The reaction was allowed to cool and then was partitioned between ethyl acetate and water. The organics were washed sequentially with water, aq sat'd NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography to afford 16.9 g (90%) of the title compound.

Aufarbeitung

  1. temperatureto cool
  2. customwas partitioned between ethyl acetate and water
  3. washThe organics were washed sequentially with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5ad771bd5b564352bf233dcaab2d6fed
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618980B2

Notizen zur Reaktion

Wird geladen…