Ammonia → 2-Methyl-5-[4-(4-propylcyclohexyl)phenyl]selenophene

HRID 1873387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1873387
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[Se:17][CH:18]=[CH:19][CH:20]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[Li][CH2:22]CCC.CI.[Cl-].[NH4+].N.Cl>C(OCC)C>[CH3:22][C:18]1[Se:17][C:16]([C:13]2[CH:14]=[CH:15][C:10]([CH:7]3[CH2:6][CH2:5][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:9][CH2:8]3)=[CH:11][CH:12]=2)=[CH:20][CH:19]=1

Komponenten

8

Edukt 6

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 594562962-[4-(4-Propylcyclohexyl)phenyl]selenopheneHCID 178418339Butyllithium

Produkt 1

HCID 594563142-Methyl-5-[4-(4-propylcyclohexyl)phenyl]selenophene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

3.4 g (10.3 mmol) of 2-[4-(4-propylcyclohexyl)phenyl]selenophene are initially introduced in 100 ml of diethyl ether, and 9.0 ml (14.3 mmol, 15% soln. in hexane) of n-BuLi are metered in rapidly. The mixture is heated under reflux for 25 min and subsequently cooled to −78° C. 1.60 ml (25.7 mmol) of methyl iodide are added in one portion, and the mixture is warmed to RT and stirred for 24 h. Sat. ammonium chloride soln. and conc. ammonia soln. are added, and the batch is stirred vigorously for a few minutes. The mixture is acidified using hydrochloric acid, and the organic phase is separated off. The aqueous phase is extracted with MTBE, and the combined organic phases are dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, n-heptane:EtOAc=25:1). The further purification is carried out by recrystallisation from ethanol and n-heptane. 2-Methyl-5-[4-(4-propylcyclohexyl)phenyl]selenophene is obtained as a colourless solid (m.p. 98° C.).

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 25 min
  3. temperaturethe mixture is warmed to RT
  4. additionare added
  5. stirringthe batch is stirred vigorously for a few minutes
  6. customthe organic phase is separated off
  7. extractionThe aqueous phase is extracted with MTBE
  8. customthe combined organic phases are dried
  9. concentrationThe solution is concentrated to dryness
  10. customthe residue is purified by column chromatography (SiO2, n-heptane:EtOAc=25:1)
  11. customThe further purification
  12. customis carried out by recrystallisation from ethanol and n-heptane

Quellen und Nachweise

ORD-Eintrag
ord-ad7689ea8bd64516afcbc3bf05a564f6
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304036B2

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