1-Bromo-3-methylbutane → 2,2,6-Trimethylheptan-3-one

HRID 358929Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 358929
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH2:8]([Mg]Br)[CH2:9][CH:10]([CH3:12])[CH3:11].[Mg].C(Br)CC(C)C>CCOCC.[Cu]I>[CH3:3][C:2]([CH3:5])([C:1](=[O:6])[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH3:4]

Komponenten

7

Edukt 4

HCID 78911-Bromo-3-methylbutaneHCID 62493Pivaloyl chlorideHCID 5462224MagnesiumHCID 178418529HCID 178418529, Verbindung

Produkt 1

HCID 200655012,2,6-Trimethylheptan-3-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a stirred mixture of pivaloyl chloride (6.02 g, 0.05 m) and copper (I) iodide (0.10 g, 0.6 mm) in dry ether (50 mls) at -60° C. under nitrogen was added dropwise isoamyl magnesium bromide [prepared from magnesium turnings (1.8 g, 0.075 m) and isoamyl bromide (7.55 g, 0.05 m) in dry ether (70 mls]. The cooling bath was removed and the reaction mixture stirred for 16 hours then poured cautiously into ice-cold dilute hydrochloric acid and extracted with ether. The combined ethereal extracts were washed with saturated aqueous sodium hydrogen carbonate solution, brine, dried (anhydrous MgSO4) and evaporated. The residue was chromatographed on silica using gradient elution (dichloromethane (0-30%) in petrol) to give the ketone as a pale yellow oil.

Aufarbeitung

  1. customThe cooling bath was removed
  2. additionthen poured cautiously into ice-cold dilute hydrochloric acid
  3. extractionextracted with ether
  4. washThe combined ethereal extracts were washed with saturated aqueous sodium hydrogen carbonate solution, brine
  5. dry with materialdried (anhydrous MgSO4)
  6. customevaporated
  7. customThe residue was chromatographed on silica using gradient elution (dichloromethane (0-30%) in petrol)

Quellen und Nachweise

ORD-Eintrag
ord-61f54d5fe4e848dba641db799bb2c6fb
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US04999043

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