Ethyl Acetate → HCID 70025127, Verbindung

HRID 1169487

Reaktionsgleichung

Reaktionsgleichung von HRID 1169487
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)C=O)[CH2:2][CH3:3].[C:13]1(P(=CC(OC)=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:37]([O:40][CH2:41][CH3:42])(=[O:39])[CH3:38]>C1(C)C=CC=CC=1>[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:7][C:6]=1[CH:13]=[CH:38][C:37]([O:40][CH2:41][CH3:42])=[O:39])[CH2:2][CH3:3]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 27604693-Propoxybenzaldehyde

Produkt 1

HCID 70025127HCID 70025127, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

3-Propoxybenzaldehyde (15.47 g) and methyl (triphenylphosphoranylidene)acetate was suspended in toluene (150 ml), and the resulting suspension was heated at reflux for 2 hours. The reaction mixture was diluted with ethyl acetate and was washed respectively with water and an aqueous saturated solution of sodium chloride, and the organic layer was dried with anhydrous magnesium sulfate. After concentration under reduced pressure to remove the solvent, the precipitated triphenylphosphine oxide was removed and was washed with ether. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain ethyl 2-propoxycinnamate (21.24 g) as a yellow oil.

Aufarbeitung

  1. temperaturethe resulting suspension was heated
  2. temperatureat reflux for 2 hours
  3. washwas washed respectively with water
  4. dry with materialan aqueous saturated solution of sodium chloride, and the organic layer was dried with anhydrous magnesium sulfate
  5. concentrationAfter concentration under reduced pressure
  6. customto remove the solvent
  7. customthe precipitated triphenylphosphine oxide was removed
  8. washwas washed with ether
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1)

Quellen und Nachweise

ORD-Eintrag
ord-79f82c2c58ee452889c778c313e383ac
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06627651B1

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