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

HRID 358929ノート

反応式

HRID 358929 の反応式
[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]

参加物

7

反応物 4

HCID 78911-Bromo-3-methylbutaneHCID 62493Pivaloyl chlorideHCID 5462224MagnesiumHCID 178418529HCID 178418529、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 3283Diethyl Ether溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-61f54d5fe4e848dba641db799bb2c6fb
出典データセット
uspto-grants-1991_03
特許番号
US04999043

反応ノート

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