Ethanol → Ethyl 3-methoxybenzoylformate

HRID 1966649Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1966649
[Se](=O)=[O:2].Br[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)=[O:7].[CH2:16]([OH:18])[CH3:17]>>[CH3:15][O:14][C:10]1[CH:9]=[C:8]([C:6](=[O:7])[C:5]([O:18][CH2:16][CH3:17])=[O:2])[CH:13]=[CH:12][CH:11]=1

Komponenten

4

Edukt 3

HCID 702EthanolHCID 24007Selenium DioxideHCID 101294Bromomethyl 3-methoxyphenyl ketone

Produkt 1

HCID 2758863Ethyl 3-methoxybenzoylformateAusbeute 53 %

Versuchsvorschrift

A suspension of selenium dioxide (4.08 g, 37 mmol) in ethanol (35 mL) was refluxed for 10 minutes and then, Intermediate 65 (8.44 g, 37 mmol) was added. The mixture was refluxed overnight. The cooled reaction was filtered through Celite and the solvent removed under reduced pressure. The residue was diluted with methylene chloride (50 mL), washed with water (2×25 mL), dried (Na2SO4), and concentrated. Purification by column chromatography with silica gel using methylene chloride as eluent gave the title compound (4.12 g, 53%) as oil.

Aufarbeitung

  1. temperaturewas refluxed for 10 minutes
  2. temperatureThe mixture was refluxed overnight
  3. customThe cooled reaction
  4. filtrationwas filtered through Celite
  5. customthe solvent removed under reduced pressure
  6. additionThe residue was diluted with methylene chloride (50 mL)
  7. washwashed with water (2×25 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customPurification by column chromatography with silica gel

Quellen und Nachweise

ORD-Eintrag
ord-df3ecd2693b84504af0e60417e53918a
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420669B2

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