Water → 4-Tert-butyl-2-(2-oxo-2-phenylethyl)-cyclohexanone

HRID 2244303

Reaktionsgleichung

Reaktionsgleichung von HRID 2244303
[C:1]([CH:5]1[CH2:10][CH2:9][C:8](N2CCCC2)=[CH:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19].[OH2:26]>CN(C=O)C>[C:1]([CH:5]1[CH2:6][CH2:7][C:8](=[O:26])[CH:9]([CH2:17][C:18](=[O:19])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:10]1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 962WaterHCID 6259Phenacyl bromideHCID 1072321-[4-(Tert-butyl)-1-cyclohexen-1-YL]pyrrolidine

Produkt 1

HCID 122703414-Tert-butyl-2-(2-oxo-2-phenylethyl)-cyclohexanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a 250-mL round-bottomed flask containing 3.3 mL of 1-(4-tert-butylcyclohex-1-enyl)pyrrolidine was added 100 mL anhydrous DMF, under nitrogen. The flask was fitted with an addition funnel containing 2-bromoacetophenone (4.12 gm) in 35 mL anhydrous DMF, which was dripped into the enamine solution over 60 min. This solution was stirred at ambient temperature for 10 hr, then 90 mL water was added to the solution and it was stirred for another 11 hr, under nitrogen. The solution was then extracted twice with ethyl acetate and water, the organic layers combined and further washed with water (3×), dried over sodium sulfate, filtered and rotovapped down to give a yellow oil. The oil was purified by MPLC using 10% ethyl acetate/hexanes.

Aufarbeitung

  1. customThe flask was fitted with an addition funnel
  2. stirringwas stirred for another 11 hr, under nitrogen
  3. extractionThe solution was then extracted twice with ethyl acetate and water
  4. washfurther washed with water (3×)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customto give a yellow oil
  8. customThe oil was purified by MPLC

Quellen und Nachweise

ORD-Eintrag
ord-439f3633dea946dead212158af3f723c
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678823B2

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