Benzyl Alcohol → Benzyl 4,4-dimethoxy-3-oxobutyrate

HRID 1700335Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1700335
[CH3:1][O:2][CH:3]([O:12][CH3:13])[C:4](=[O:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].C(O)[C:15]1[CH:20]=[CH:19]C=[CH:17][CH:16]=1.P([O-])([O-])([O-])=O>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[CH3:1][O:2][CH:3]([O:12][CH3:13])[C:4](=[O:11])[CH2:5][C:6]([O:8][CH2:9][C:10]1[CH:19]=[CH:20][CH:15]=[CH:16][CH:17]=1)=[O:7]

Komponenten

6

Edukt 3

HCID 244Benzyl AlcoholHCID 1061PhosphateHCID 248327Ethyl 4,4-dimethoxy-3-oxobutanoate

Produkt 1

HCID 18318278Benzyl 4,4-dimethoxy-3-oxobutyrate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

2.68 g (14.1 mmol) of ethyl 4,4-dimethoxy-3-oxo-butyrate, 3.62 ml (34.9 mmol) of benzyl alcohol and 244 mg (2.0 mmol) of 4-dimethylaminopyridine were heated under reflux in 40 ml of toluene for three nights. A phosphate buffer solution was added to the obtained reaction solution. After the extraction with ethyl acetate, the organic layer was washed with a saturated aqueous salt solution and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by the silica gel chromatography (hexane/ethyl acetate=9:1) to obtain the title compound.

Aufarbeitung

  1. extractionAfter the extraction with ethyl acetate
  2. washthe organic layer was washed with a saturated aqueous salt solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by the silica gel chromatography (hexane/ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-5528c3d14ce94083a61c9fa6555a229c
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06350762B1

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