1-Phenyl-8-(2-tetrahydropyranyloxy)-1-octyne → (E)-8-phenyl-7-octen-1-ol

HRID 477008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 477008
[C:1]1([C:7]#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15]C2CCCCO2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.COCCOCCOC>[C:1]1(/[CH:7]=[CH:8]/[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 148342201-Phenyl-8-(2-tetrahydropyranyloxy)-1-octyneHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 14834222(E)-8-phenyl-7-octen-1-olAusbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21261944Tetrahydrofuran diglymeLösungsmittel

Versuchsvorschrift

To 150 ml of a mixture of tetrahydrofuran-diglyme (2:15) were added 12 g of 1-phenyl-8-(2-tetrahydropyranyloxy)-1-octyne and 3.35 g of lithium aluminum hydride. The mixture was heated and tetrahydrofuran was distilled off until the inner temperature became 120° C. After heating under reflux at the same temperature for 1 hour, the mixture was ice-cooled. Ice was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with 10% hydrochloric acid, water, sodium hydrogen carbonate solution, saline water in the order mentioned, dried, and then the solvent was distilled off. The residue was dissolved in 250 ml of methanol and 1.1 g of p-toluenesulfonic acid was added thereto. The mixture was stirred at room temperature for 1 hour and 2 ml of triethylamine was added to the mixture. Methanol was distilled off and the residue was purified by silica gel column chromatorgraphy (solvent: hexane-ethyl acetate=3:1) to give 7.5 g of (E)-8-phenyl-7-octen- 1-ol as an oily substance.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. distillationtetrahydrofuran was distilled off until the inner temperature
  3. custombecame 120° C
  4. temperatureAfter heating
  5. temperatureunder reflux at the same temperature for 1 hour
  6. temperaturecooled
  7. additionIce was added to the mixture
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe organic layer was washed with 10% hydrochloric acid, water, sodium hydrogen carbonate solution, saline water in the order
  10. customdried
  11. distillationthe solvent was distilled off
  12. dissolutionThe residue was dissolved in 250 ml of methanol
  13. addition1.1 g of p-toluenesulfonic acid was added
  14. addition2 ml of triethylamine was added to the mixture
  15. distillationMethanol was distilled off
  16. customthe residue was purified by silica gel column chromatorgraphy (solvent: hexane-ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-d83d674862434502869601ae7dc865a0
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04886817

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