Hydrochloric Acid → HCID 59456263, Verbindung

HRID 1873421

Reaktionsgleichung

Reaktionsgleichung von HRID 1873421
[Se:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Li]CCCC.[CH2:11]([CH:14]1[CH2:19][CH2:18][CH:17]([CH:20]2[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]2)[CH2:16][CH2:15]1)[CH2:12][CH3:13].[Cl-].[NH4+].Cl>C(OCC)C>[CH2:11]([CH:14]1[CH2:19][CH2:18][CH:17]([CH:20]2[CH2:21][CH2:22][C:23]([C:2]3[Se:1][CH:5]=[CH:4][CH:3]=3)([OH:26])[CH2:24][CH2:25]2)[CH2:16][CH2:15]1)[CH2:12][CH3:13]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 136130SelenopheneHCID 4354185[1,1'-Bicyclohexyl]-4-one,4'-propyl-,HCID 178418339Butyllithium

Produkt 1

HCID 59456263HCID 59456263, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
-50 °C

Versuchsvorschrift

25.0 g (0.19 mol) of selenophene are initially introduced in 250 ml of diethyl ether, and 130 ml (0.21 mol, 15% soln. in hexane) of n-BuLi are added. The mixture is warmed under reflux for 25 min and subsequently cooled to −50° C. A solution of 46.7 g (0.21 mol) of 4′-propylbicyclohexyl-4-one in 70 ml of diethyl ether is metered in, and the mixture is slowly warmed to RT. After 18 h, sat. ammonium chloride soln. and 2 N hydrochloric acid are added, and the organic phase is separated off. The aqueous phase is extracted with diethyl ether, and the combined organic phase is washed with 1 N hydrochloric acid and sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:EtOAc=3:1→2:1). Further purification is carried out by recrystallisation from n-heptane. 4′-Propyl-4-selenophen-2-ylbicyclohexyl-4-ol is obtained as a yellow-brown solid.

Aufarbeitung

  1. temperatureThe mixture is warmed
  2. temperatureunder reflux for 25 min
  3. temperatureis slowly warmed to RT
  4. customthe organic phase is separated off
  5. extractionThe aqueous phase is extracted with diethyl ether
  6. washthe combined organic phase is washed with 1 N hydrochloric acid and sat. sodium chloride soln
  7. customThe solution is dried
  8. concentrationconcentrated to dryness
  9. customThe residue is purified by column chromatography (SiO2, n-heptane:EtOAc=3:1→2:1)
  10. customFurther purification
  11. customis carried out by recrystallisation from n-heptane

Quellen und Nachweise

ORD-Eintrag
ord-df76d5a1dcdc4ca2b1f9a2faca55b63e
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304036B2

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