p-METHYLACETOPHENONE → alpha-Cyclopropyl-alpha,4-dimethylbenzenemethanol

HRID 561461

反応式

HRID 561461 の反応式
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=1>C1COCC1.C(OCC)C>[CH:1]1([C:13]([C:10]2[CH:11]=[CH:12][C:7]([CH3:6])=[CH:8][CH:9]=2)([OH:15])[CH3:14])[CH2:3][CH2:2]1

参加物

5

反応物 2

HCID 8500p-METHYLACETOPHENONEHCID 178418630HCID 178418630、化合物2 回

生成物 1

HCID 98258alpha-Cyclopropyl-alpha,4-dimethylbenzenemethanol

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

27 ml (26.8 mmol) of 1N cyclopropylmagnesium bromide solution in THF were added to 3.00 g (22.4 mmol) of 1-(4-methylphenyl)ethanone in 60 ml of diethyl ether at RT, and the mixture was stirred at RT overnight. Then a further 11 ml (11.2 mmol) of 1N cyclopropylmagnesium bromide solution in THF were added, and the mixture was stirred at RT overnight. The reaction mixture was added to ice-water, the phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate gradient with addition of 0.1% triethylamine) to result in 491 mg (13% of theory) of the title compound.

後処理

  1. stirringthe mixture was stirred at RT overnight
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate gradient with addition of 0.1% triethylamine)

出典と根拠

ORDレコード
ord-c1709cb70138446aa871527e8b3fb398
出典データセット
uspto-grants-2011_11
特許番号
US08063234B2

関連ノート

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