Acetic Acid → Ethyl 2-benzyl-3-oxopropanoate

HRID 705823

Reaktionsgleichung

Reaktionsgleichung von HRID 705823
[H-].[Na+].[C:3]1([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:16](OCC)=[O:17].C(O)(=O)C>COCCOC>[CH:16]([CH:10]([CH2:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:17]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8025Ethyl formateHCID 16237Ethyl 3-phenylpropionateHCID 24758Sodium hydride

Produkt 1

HCID 562571Ethyl 2-benzyl-3-oxopropanoateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of NaH (2.338 g, 58.5 mmol) in DME (20 mL) was added dropwise a solution of ethyl 3-phenylpropanoate (3.2 g, 19.49 mmol) and ethyl formate (6.28 mL, 78 mmol) in DME (20 mL) at room temperature. The reaction mixture was then stirred overnight. It was neutralized with acetic acid (4 mL), then extracted with EtOAc. The organic phase was collected, washed with brine, dried over Na2SO4, filtered, and concentrated affording the crude title compound (4.02 g, 100% yield). LCMS: rt=2.82 and 3.51 min (a mixture of ketone and enol isomer), [M+H+]=207.1

Aufarbeitung

  1. extractionextracted with EtOAc
  2. customThe organic phase was collected
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7f8a389c3bc0491d9d17997fc27404b0
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174968B2

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