2,2-Dimethyl-3-heptanol → 2,2-Dimethyl-3-heptanone

HRID 229971ノート

反応式

HRID 229971 の反応式
[CH3:1][C:2]([CH3:10])([CH:4]([OH:9])[CH2:5][CH2:6][CH2:7][CH3:8])[CH3:3].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:1][C:2]([CH3:10])([C:4](=[O:9])[CH2:5][CH2:6][CH2:7][CH3:8])[CH3:3]

参加物

4

反応物 2

HCID 1405432,2-Dimethyl-3-heptanolHCID 178418287HCID 178418287、化合物

生成物 1

HCID 1404722,2-Dimethyl-3-heptanone収率 89.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2,2-Dimethyl-heptan-3-ol (0.23 mol) was dissolved in 350 mL of CH2Cl2 in a 500 mL round bottom flask with a magnetic stirbar. The flask was partially cooled with ice. 76.6 g (0.355 mol) of pyridinium chlorochromate was added, while vigorously stirring. The reaction turned black and warmed up slightly. The reaction mixture was stirred at room temperature for 24 hours. The solution was decanted away from the black sludge, which was rinsed with hexane. The organic extracts were combined and chromatographed directly on silica gel. (Note: only silica has been found to trap and remove the reduced non-reacted chromium compounds). The product, 2,2-dimethyl-heptan-3-one, eluted with CH2Cl2/hexane and in a subsequent 10% ethyl acetate/hexane fraction to yield 29.19 g of product at 88% yield. 1H NMR (CDCl3, 500 MHz) δ (ppm): 2.48 (t, 2H), 1.54 (m, 2H), 1.28 (m, 2H), 1.13 (s, 9H), 0.90 (m, 3H).

後処理

  1. temperatureThe flask was partially cooled with ice
  2. temperaturewarmed up slightly
  3. stirringThe reaction mixture was stirred at room temperature for 24 hours
  4. customThe solution was decanted away from the black sludge, which
  5. washwas rinsed with hexane
  6. customchromatographed directly on silica gel
  7. custom(Note: only silica has been found to trap
  8. customremove the reduced non-reacted chromium compounds)
  9. washThe product, 2,2-dimethyl-heptan-3-one, eluted with CH2Cl2/hexane and in a subsequent 10% ethyl acetate/hexane fraction

出典と根拠

ORDレコード
ord-dad9c9c6fa804d0d93a1eef9f593a779
出典データセット
uspto-grants-2009_07
特許番号
US07563928B2

反応ノート

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