Acetic Acid → HCID 86755685, Verbindung

HRID 1872394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1872394
[H-].[Na+].[C:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)(=O)[CH3:4].[C:25]([OH:28])(=[O:27])[CH3:26].O1CC[CH2:31][CH2:30]1>>[CH2:18]([C:15]1[CH:16]=[CH:17][C:12]([C:9]2[CH:10]=[CH:11][C:6](/[C:3](/[CH3:4])=[CH:26]/[C:25]([O:28][CH2:30][CH3:31])=[O:27])=[CH:7][CH:8]=2)=[CH:13][CH:14]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Komponenten

5

Edukt 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 11208635HCID 11208635, Verbindung

Produkt 1

HCID 86755685HCID 86755685, Verbindung

Versuchsvorschrift

To a suspension of sodium hydride (60% in oil, 0.37 g) in tetrahydrofuran (40 ml) was added by portions 4-acetyl-4'-n-heptylbiphenyl (2.50 g) at ambient temperature. After stirring at ambient temperature for 1 hour, to the solution was added triethyl phosphonoacetate (1.9 ml) and the mixture was heated to reflux for 5 hours. After cooling to ambient temperature, to the mixture was added acetic acid (0.53 ml) and evaporated. The residue was taken up into a mixture of water and ethyl acetate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (200 ml) eluting with mixture of n-hexane and diisopropyl ether (99:1-20:1, V/V) to give Ethyl (E)-3-[4-(4-heptylphenyl)phenyl]-2-butenoate (2.19 g).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 5 hours
  3. temperatureAfter cooling to ambient temperature, to the mixture
  4. customevaporated
  5. additionThe residue was taken up into a mixture of water and ethyl acetate
  6. washThe separated organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customThe residue was chromatographed on silica gel (200 ml)
  10. washeluting with mixture of n-hexane and diisopropyl ether (99:1-20:1, V/V)

Quellen und Nachweise

ORD-Eintrag
ord-399f0cb67a604698a01a57da3cc6d975
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06107458

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