Ethyl Acetate → HCID 22759289, Verbindung

HRID 460848Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 460848
[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-548d4428fce841fb8071c0388cfc34bf
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04061643

Notizen zur Reaktion

Wird geladen…