Sodium Iodide → 4-(3,5-Dimethylbenzyl)-3,5-heptanedione

HRID 353092

Reaktionsgleichung

Reaktionsgleichung von HRID 353092
[CH3:1][CH2:2][C:3](=[O:9])[CH2:4][C:5](=[O:8])[CH2:6][CH3:7].[H-].[Na+].[I-].[Na+].[CH3:14][C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([CH3:23])[CH:22]=1)[CH2:18]Br>CC(=O)CC>[CH3:14][C:15]1[CH:22]=[C:21]([CH:20]=[C:17]([CH3:18])[CH:16]=1)[CH2:23][CH:4]([C:3](=[O:9])[CH2:2][CH3:1])[C:5](=[O:8])[CH2:6][CH3:7]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 819233,5-HeptanedioneHCID 1413343,5-Dimethylbenzyl bromide

Produkt 1

HCID 218770904-(3,5-Dimethylbenzyl)-3,5-heptanedioneAusbeute 44,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A solution of 3,5-heptanedione (1.24 ml, 9.13 mmol) in 2-butanone (40 ml) was treated with sodium hydride (60% dispersion in oil) (402 mg, 10.05 mmol) (added in portions) and stirred at room temperature for 10 minutes. Sodium iodide (1.5 g, 10.05 mmol) and then by 3,5-dimethylbenzyl bromide (2.0 g, 10.05 mmol) were added to the reaction mixture which was stirred at room temperature for 18 hours. The solution was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with water (×3). The organic phase was dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with cyclohexane followed by cyclohexane:ethyl acetate (40:1, by volume) to afford the title compound as a yellow oil (995 mg).

Aufarbeitung

  1. stirringwas stirred at room temperature for 18 hours
  2. concentrationThe solution was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water (×3)
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude product was purified by flash chromatography on silica gel eluting with cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-ab3a1917d80c43939eecc3561cd7ad4e
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06750230B2

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