Water → 1-Cyclopropyl-1-(2,4-difluorophenyl)ethanol

HRID 561416ノート

反応式

HRID 561416 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[CH:12]1([Mg]Br)[CH2:14][CH2:13]1.O.C(OCC)(=O)C>C(OCC)C.O1CCCC1>[CH:12]1([C:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])([OH:11])[CH3:10])[CH2:14][CH2:13]1

参加物

7

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 677702,4-DifluoroacetophenoneHCID 178418630HCID 178418630、化合物

生成物 1

HCID 247496791-Cyclopropyl-1-(2,4-difluorophenyl)ethanol

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

1.50 g (9.61 mmol) of 2′,4′-difluoroacetophenone were dissolved at 0° C. in 8 ml of diethyl ether, and 38.4 ml (19.21 mmol) of a 0.5N solution of cyclopropylmagnesium bromide in tetrahydrofuran were slowly added dropwise. Stirring at 0° C. for 1 h was followed by warming to RT, and the reaction solution was mixed with water and ethyl acetate, and the phases were separated. The organic phase was washed with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the solvents were removed in vacuo. The crude product was purified by preparative HPLC (mobile phase: acetonitrile-water gradient) to result in 0.63 g (33% of theory) of the title compound.

後処理

  1. temperatureby warming to RT
  2. customthe phases were separated
  3. washThe organic phase was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customthe solvents were removed in vacuo
  6. customThe crude product was purified by preparative HPLC (mobile phase: acetonitrile-water gradient)

出典と根拠

ORDレコード
ord-52d7e875ed7d481392633e4421a1c829
出典データセット
uspto-grants-2011_11
特許番号
US08063234B2

反応ノート

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