3,5-Dimethylcyclohex-2-en-1-one → 3-Benzyl-3,5-dimethylcyclohexanone

HRID 1292945

反応式

HRID 1292945 の反応式
[CH2:1]([Mg]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][C:11]1[CH2:16][CH:15]([CH3:17])[CH2:14][C:13](=[O:18])[CH:12]=1>C(OCC)C.Cl[Cu]>[CH2:1]([C:11]1([CH3:10])[CH2:16][CH:15]([CH3:17])[CH2:14][C:13](=[O:18])[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 142913,5-Dimethylcyclohex-2-en-1-oneHCID 178419663HCID 178419663、化合物

生成物 1

HCID 222215123-Benzyl-3,5-dimethylcyclohexanone収率 53%

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 3283Diethyl Ether溶媒2 回

実験手順

To a cooled (−20° C.) 1M benzylmagnesium bromide solution in diethyl ether (50 ml) under argon was added CuCl (0.52 g, 5.3 mmol) and the mixture was stirred for 5 min. Then a solution of 3,5-dimethyl-2-cyclohexen-1-one (12) (4.4 g, 35.1 mmol) in diethyl ether (15 ml) was added dropwise keeping the temperature below −10° C. The mixture was stirred for 2 h and quenched with 10% aqueous acetic acid (40 ml). The organic layer was separated, washed with water, saturated aqueous NaHCO3 and saturated aqueous NaCl, and dried over MgSO4. Filtration and concentration in vacuo afforded oily residue what was separated by flash chromatography on silica gel (light petroleum ether-ethyl acetate, 10:1). Cyclohexanone 13 (4.0 g, 53%) was obtained as a colorless oil.

後処理

  1. customthe temperature below −10° C
  2. stirringThe mixture was stirred for 2 h
  3. customquenched with 10% aqueous acetic acid (40 ml)
  4. customThe organic layer was separated
  5. washwashed with water, saturated aqueous NaHCO3 and saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. filtrationFiltration and concentration in vacuo
  8. customafforded oily residue what
  9. customwas separated by flash chromatography on silica gel (light petroleum ether-ethyl acetate, 10:1)

出典と根拠

ORDレコード
ord-c9f41d6b88b5409598f51df05bedfef2
出典データセット
uspto-grants-2007_07
特許番号
US07238703B2

関連ノート

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