Acetic Acid → Ethyl 3-[3-(benzyloxy)phenyl]-3-oxopropanoate

HRID 17883

Reaktionsgleichung

Reaktionsgleichung von HRID 17883
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15](=[O:17])[CH3:16])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].C(O)(=O)C.[C:24](=O)([O:28]CC)[O:25][CH2:26][CH3:27]>>[CH2:26]([O:25][C:24](=[O:28])[CH2:16][C:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1)=[O:17])[CH3:27]

Komponenten

5

Edukt 4

HCID 176Acetic AcidHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 986891-(3-(Phenylmethoxy)phenyl)ethan-1-one

Produkt 1

HCID 10334847Ethyl 3-[3-(benzyloxy)phenyl]-3-oxopropanoateAusbeute 84 %

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

1-(3-Benzyloxyphenyl)ethanone (218 g, 966.10 mmol) was dissolved in diethyl carbonate and sodium hydride (60% oil) (46.37 g, 1.15 mmol) was slowly added thereto at 0° C., and then stirred for 3 hours at 60° C. After the reaction was completed, ice water and acetic acid were added to the reaction mixture, extracted with ethyl acetate/saturated sodium chloride, the organic layer was separated, and dried over anhydrous magnesium sulfate. The solvent was removed under a reduced pressure and the resulting residue was purified by column chromatography (ethyl acetate:hexane=1:10) to obtain 3-(3-benzyloxyphenyl)-3-oxopropionate ethyl ester (184.68 g, yield 84%) in an oil state.

Aufarbeitung

  1. extractionextracted with ethyl acetate/saturated sodium chloride
  2. customthe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under a reduced pressure
  5. customthe resulting residue was purified by column chromatography (ethyl acetate:hexane=1:10)

Quellen und Nachweise

ORD-Eintrag
ord-444829afa1d64032803c8a8149fb905d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741323B2

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