Benzyl Bromide → Diethyl 2-benzyl-3-oxopentanedioate

HRID 45235

Reaktionsgleichung

Reaktionsgleichung von HRID 45235
[Na].[O:2]=[C:3]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCO>[CH2:16]([CH:10]([C:3](=[O:2])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 66045Diethyl acetonedicarboxylateHCID 5360545Sodium

Produkt 1

HCID 12200242Diethyl 2-benzyl-3-oxopentanedioateAusbeute 38,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Under argon, and at room temperature, 1.7 g (74.18 mmol) of sodium are dissolved in 75 mL of anhydrous EtOH. 13.5 mL (74.2 mmol) of diethyl 3-oxopentanedioate and then 8.8 mL (74.2 mmol) of benzyl bromide are then added dropwise, at room temperature. The medium is then refluxed for 3 hours, concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 20% EtOAc. 8.29 g of diethyl 2-benzyl-3-oxopentanedioate are obtained in the form of a translucent oil.

Aufarbeitung

  1. temperatureThe medium is then refluxed for 3 hours
  2. concentrationconcentrated under reduced pressure
  3. custompurified by chromatography on a column of silica gel
  4. washeluting with a cyclohexane/EtOAc gradient of 0 to 20% EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-24d77ef71b8d49cca9a94a51e129b70c
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541455B2

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