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

HRID 561416

Reaktionsgleichung

Reaktionsgleichung von HRID 561416
[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

Komponenten

7

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 677702,4-DifluoroacetophenoneHCID 178418630HCID 178418630, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-52d7e875ed7d481392633e4421a1c829
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063234B2

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