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

HRID 1794191

반응식

HRID 1794191 반응식
[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

참가 물질

5

반응물 2

HCID 142913,5-Dimethylcyclohex-2-en-1-oneHCID 178419663HCID 178419663, 화합물

생성물 1

HCID 222215123-Benzyl-3,5-dimethylcyclohexanone수율 53%

시약·촉매·용매 2

HCID 62652Cuprous chloride촉매HCID 3283Diethyl Ether용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-600839a88a0b4a06ba14a9cfd5d75e29
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022729B2

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