Ethyl bromoacetate → 4-(4-Methoxy-phenyl)-4-oxo-3-phenyl-butyric acid ethyl ester

HRID 887006

Reaktionsgleichung

Reaktionsgleichung von HRID 887006
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:19])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1.Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CS(C)=O.C1(C)C=CC=CC=1>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][CH:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:11]([C:8]1[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:10][CH:9]=1)=[O:19])[CH3:26]

Komponenten

6

Edukt 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 2310931-(4-Methoxyphenyl)-2-phenylethan-1-one

Produkt 1

HCID 134415094-(4-Methoxy-phenyl)-4-oxo-3-phenyl-butyric acid ethyl esterAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A suspension of NaH (12.8 mmol, 512 mg) in DMSO (23 mL) was added 4′-methoxy-2-phenylacetophenone (12.8 mmol, 2.89 g) in 10 ml toluene dropwise under argon. After 30 minutes of stirring, ethyl bromoacetate (1.4 mL, 1 eq.) in 10 mL of toluene was added and the mixture was stirred at rt overnight. The reaction was quenched by addition of 2N HCl (4 mL), and then 60 mL of water. The mixture was extracted with CH2Cl2 (3×30 mL), dried over MgSO4 and concentrated under vacuum overnight to afforded 4.0 g (99%) of 4-(4-methoxy-phenyl)-4-oxo-3-phenyl-butyric acid ethyl ester.

Aufarbeitung

  1. stirringthe mixture was stirred at rt overnight
  2. customThe reaction was quenched by addition of 2N HCl (4 mL)
  3. extractionThe mixture was extracted with CH2Cl2 (3×30 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-1a501fcd1f934606885534729d3b3c5d
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247414B2

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