Sodium Iodide → HCID 49765294, Verbindung

HRID 537671Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 537671
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:16][CH3:17])=[C:6]([CH:8]2[C:13](=[O:14])[CH2:12][CH2:11][CH2:10][C:9]2=[O:15])[CH:7]=1.[I-:18].[Na+].C[Si](C)(C)N[Si](C)(C)C.CN(C)[C@@H]1CCCC[C@H]1N>[Cu]I.O1CCOCC1>[CH2:16]([C:5]1[CH:4]=[CH:3][C:2]([I:18])=[CH:7][C:6]=1[CH:8]1[C:13](=[O:14])[CH2:12][CH2:11][CH2:10][C:9]1=[O:15])[CH3:17]

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 13838HexamethyldisilazaneHCID 11275066(1R,2R)-N1,N1-Dimethylcyclohexane-1,2-diamineHCID 49765293HCID 49765293, Verbindung

Produkt 1

HCID 49765294HCID 49765294, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

To a mixture of 2-(5-bromo-2-ethylphenyl)cyclohexane-1,3-dione (0.917 g, 3.11 mmol), sodium iodide (0.934 g, 6.23 mmol) and hexamethyldisilazane (0.454 g, 3.11 mmol) is added copper (I) iodide (0.030 g, 0.15 mmol) and trans-N,N-dimethyl-1,2-cyclohexane diamine (0.044 g, 0.31 mmol). Degassed dioxane (5 ml) is added and the mixture is purged with nitrogen then heated at 180° C. for 1 hour under microwave irradiation. After cooling to room temperature the reaction mixture is treated with 2M aqueous hydrochloric acid and extracted with dichloromethane. The phases are separated and the aqueous phase is further extracted with dichloromethane. Organic fractions are combined then evaporated under reduced pressure to yield a crude product which is purified by flash column chromatography (10% ethyl acetate/hexane to 70% ethyl acetate/hexane eluant) to afford 2-(2-ethyl-5-iodophenyl)cyclohexane-1,3-dione as a white foam.

Aufarbeitung

  1. customthe mixture is purged with nitrogen
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. additionis treated with 2M aqueous hydrochloric acid
  4. extractionextracted with dichloromethane
  5. customThe phases are separated
  6. extractionthe aqueous phase is further extracted with dichloromethane
  7. customOrganic fractions are combined then evaporated under reduced pressure
  8. customto yield a crude product which
  9. customis purified by flash column chromatography (10% ethyl acetate/hexane to 70% ethyl acetate/hexane eluant)

Quellen und Nachweise

ORD-Eintrag
ord-87d2f789a9394e3680500b84f128f3e8
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865623B2

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