4-Nitrobenzyl bromide → Diethyl 2-(4-nitrobenzyl)-2-methylmalonate

HRID 2176909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2176909
C[CH2:2][CH:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:4]([O:6][CH3:7])=[O:5].[O-][CH2:14]C.[Na+].[Na].[N+:18]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1)([O-:20])=[O:19]>CCO>[N+:18]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25][C:3]([CH3:2])([C:4]([O:6][CH2:7][CH3:14])=[O:5])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:23][CH:22]=1)([O-:20])=[O:19]

Komponenten

6

Edukt 4

HCID 660114-Nitrobenzyl bromideHCID 2723922Sodium ethoxideHCID 5088009HCID 5088009, VerbindungHCID 5360545Sodium

Produkt 1

HCID 54496963Diethyl 2-(4-nitrobenzyl)-2-methylmalonateAusbeute 29,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Diethyl methyl malonate (1.60 ml, 9.25 mmol) was added to a freshly prepared solution of sodium ethoxide solution [(sodium (212 mg, 9.25 mmol) in EtOH (20 ml)] and stirred for 1 h. 4-Nitrobenzyl bromide (2.00 g, 9.25 mmol) was added dropwise to the reaction mixture and stirred for 6 h at reflux. The reaction mixture was cooled to room temperature and concentrated. The residue was partitioned between water and CHCl3. The separated organic layer was washed with water, brine solution, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the crude product. This was purified by column chromatography over silica gel (100-200 mesh) using 5% ethyl acetate in petroleum ether as eluent to afford 850 mg (29.7%) of diethyl 2-(4-nitrobenzyl)-2-methylmalonate as oily liquid.

Aufarbeitung

  1. stirringstirred for 6 h
  2. temperatureat reflux
  3. concentrationconcentrated
  4. customThe residue was partitioned between water and CHCl3
  5. washThe separated organic layer was washed with water, brine solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give the crude product
  10. customThis was purified by column chromatography over silica gel (100-200 mesh)

Quellen und Nachweise

ORD-Eintrag
ord-f8188fccd9b744dba58d28e814b8cad1
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067888B2

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