tert-Butanol → 2-Allyl-6-[(butylthio)methylene]-2-ethylcyclohexanone

HRID 1438915Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1438915
[CH3:1][C:2](C)([O-])C.[K+].[C:7](O)(C)(C)C.[CH2:12]([S:16][CH:17]=[C:18]1[CH2:23][CH2:22][CH2:21][CH:20]([CH2:24][CH3:25])[C:19]1=[O:26])[CH2:13][CH2:14][CH3:15].C(Br)C=C>CCCCCC.CCOCC>[CH2:24]([C:20]1([CH2:1][CH3:2])[CH2:21][CH2:22][CH2:23][C:18](=[CH:17][S:16][CH2:12][CH2:13][CH2:14][CH3:15])[C:19]1=[O:26])[CH:25]=[CH2:7]

Komponenten

7

Edukt 4

HCID 6386tert-ButanolHCID 7841Allyl bromideHCID 23665647Potassium tert-butoxideHCID 537663082-[(Butylthio)methylene]-6-ethylcyclohexanone

Produkt 1

HCID 545033622-Allyl-6-[(butylthio)methylene]-2-ethylcyclohexanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a well stirred solution of potassium tert-butoxide (17.95 g, 0.16 mole) in dry redistilled tert-butanol (160 ml) nitrogen, 2-[(butylthio)methylene]-6-ethylcylcohexanone (9.05 g, 0.04 mole), described in Example 3, is added slowly. The mixture is stirred at room temperature for 5 minutes and then chilled in an ice bath. Allyl bromide (21.8 g, 0.18 mole) is added rapidly to the chilled mixture. The mixture is then stirred at room temperature for 48 hr. Most of the solvent is then removed under reduced pressure and water (about 150 ml) is added. The aqueous solution is extracted with ether (3 x). The combined ether extracts are washed with brine, dried (MgSO4) and concentrated to yield oil. The oil is subjected to chromotography on silica gel (320 g) using 4% ether in hexane as eluant. Concentration of the eluate gives 2-allyl-6-[(butylthio)methylene]-2-ethylcyclohexanone, nmr(CDCl3) δ 0.85 (t, J=7, 3H), 2.85 (t, J=7, 2H), 4.80 - 6.0 (m, 3H), 7.5 (t, J=2, 1H).

Aufarbeitung

  1. additionis added slowly
  2. temperaturechilled in an ice bath
  3. stirringThe mixture is then stirred at room temperature for 48 hr
  4. customMost of the solvent is then removed under reduced pressure and water (about 150 ml)
  5. additionis added
  6. extractionThe aqueous solution is extracted with ether (3 x)
  7. washThe combined ether extracts are washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customto yield oil

Quellen und Nachweise

ORD-Eintrag
ord-ad607d2a537d4cc48bda80b8e410ab35
Quelldatensatz
uspto-grants-1977_11
Patentnummer
US04057559

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