Ethyl Acetate → HCID 22759289, Verbindung

HRID 1730130Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1730130
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[O:13][CH2:14][C:15]#[C:16][CH:17]([OH:27])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1.C(OCC)(=O)C>CCOCC>[O:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[O:13][CH2:14]/[CH:15]=[CH:16]/[CH:17]([OH:27])[CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 22759318HCID 22759318, Verbindung

Produkt 1

HCID 22759289HCID 22759289, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Lithium aluminum hydride (7.6 g., 0.2 mole) is dissolved in ether (225 ml.) and 1-(2-tetrahydropyranyloxy)- 4-hydroxy-5-(4-fluorophenoxy)-2-pentyne (35.2 g., 0.12 mole) is added dropwise with stirring during 1.5 hour. The resulting mixture is stirred at 25° for 21 hours and then heated at reflux for 4 hours. The mixture is cooled and treated dropwise with ethyl acetate to consume excess lithium aluminum hydride. It is then poured into 600 ml. of ice-cold 20% aqueous potassium hydroxide solution. The oily product is taken up in ether, washed with water and brine, and dried over magnesium sulfate. Removal of solvent under vacuum leaves the title compound as a yellow residual oil.

Aufarbeitung

  1. stirringThe resulting mixture is stirred at 25° for 21 hours
  2. temperatureheated
  3. temperatureat reflux for 4 hours
  4. temperatureThe mixture is cooled
  5. customto consume excess lithium aluminum hydride
  6. additionIt is then poured into 600 ml
  7. washwashed with water and brine
  8. dry with materialdried over magnesium sulfate
  9. customRemoval of solvent under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-71626e27a00443238f6ea062086b83d6
Quelldatensatz
uspto-grants-1976_11
Patentnummer
US03991106

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