Hydrochloric Acid → HCID 596327, Verbindung

HRID 1903709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1903709
C([Li])CCC.[S:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.[C:11]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.Cl.CC1C=CC(S(O)(=O)=O)=CC=1>CCOCC.C1C=CC=CC=1>[C:11]1([C:7]2[S:6][CH:10]=[CH:9][CH:8]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 7967CyclohexanoneHCID 8030ThiopheneHCID 178418339Butyllithium

Produkt 1

HCID 596327HCID 596327, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

n-Butyllithium (40.7 ml, 1.5 M) was added dropwise to a stirred solution of thiophene (5 g) in dry ether (50 ml) and the mixture heated under reflux for 30 min. After cooling to -78°, cyclohexanone (6.21 ml) in dry ether (30 ml) was added dropwise and the temperature allowed to rise to ambient. After 1h 2N hydrochloric acid (80 ml) was added and stirring continued for 16h. The organic layer was separated and the aqueous layer extracted with ether (2×40 ml). The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to give an oil, which was dissolved in benzene (50 ml) and heated under reflux in the presence of PTSA for 0.75h. the cooled solution was washed twice with 8% NaHCO3 solution and the aqueous solution extracted with ether (2×40 ml), dried (MgSO4) filteed and evaporated to give the title compound as an oil (9.83 g). TLC(F) Rf 0.73

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 30 min
  3. temperatureAfter cooling to -78°
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted with ether (2×40 ml)
  6. washThe combined extracts were washed with water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customto give an oil, which
  11. temperatureheated
  12. washwas washed twice with 8% NaHCO3 solution
  13. extractionthe aqueous solution extracted with ether (2×40 ml)
  14. dry with materialdried (MgSO4)
  15. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d166e26b1a17423eb78411ad2d6d0d10
Quelldatensatz
uspto-grants-1984_03
Patentnummer
US04438111

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