Water → 1-Cyclopropyl-1-(4-fluorophenyl)ethanol

HRID 561415

Reaktionsgleichung

Reaktionsgleichung von HRID 561415
[C:1]([CH:4]1[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[F:7][C:8]1[CH:13]=[CH:12][C:11]([Mg]Br)=[CH:10][CH:9]=1.O.C(OCC)(=O)C>C(OCC)C.O1CCCC1>[CH:4]1([C:1]([C:11]2[CH:12]=[CH:13][C:8]([F:7])=[CH:9][CH:10]=2)([OH:3])[CH3:2])[CH2:6][CH2:5]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 13004Cyclopropyl methyl ketoneHCID 178418676HCID 178418676, Verbindung

Produkt 1

HCID 981041-Cyclopropyl-1-(4-fluorophenyl)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

0.50 g (5.94 mmol) of acetylcyclopropane was dissolved at 0° C. in 5 ml of diethyl ether, and 8.9 ml (8.91 mmol) of a 1N solution of 4-fluorophenylmagnesium 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 flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10/1) to result in 0.99 g (93% 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 flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10/1)

Quellen und Nachweise

ORD-Eintrag
ord-29ddf9cdef3b4eae9fb2f2c1499a76cc
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063234B2

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