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

HRID 1764884

Reaktionsgleichung

Reaktionsgleichung von HRID 1764884
C1(C2C=C(F)C=C[C:5]=2[C:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[CH:20]2[CH2:22][CH2:21]2)=O)CC1.C[Mg]Br.C1C[O:29]CC1>CCOCC>[CH:20]1([C:14]([C:13]2[CH:11]=[CH:5][C:16]([F:19])=[CH:17][CH:18]=2)([OH:29])[CH3:15])[CH2:21][CH2:22]1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 53737258Cyclopropyl-4-fluorophenyl ketoneHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 981041-Cyclopropyl-1-(4-fluorophenyl)ethanolAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of cyclopropyl-4-fluorophenyl ketone (523 mg, 3.19 mmol) in THF (10 mL) at 0° C. under N2 was added 3 M methyl magnesium bromide (1.7 mL, 5.1 mmol) in Et2O. After 90 minutes at 0° C., the reaction was quenched by addition of brine (10 mL) and diluted with Et2O (100 mL). The organic solution was washed with saturated NaHCO3 (100 mL) and brine (100 mL). Column purification (hexanes:EtOAc 9:1) yielded 1-cyclopropyl-1-(4-fluorophenyl)ethanol (512 mg, 89%) as a colorless oil.

Aufarbeitung

  1. customthe reaction was quenched by addition of brine (10 mL)
  2. additiondiluted with Et2O (100 mL)
  3. washThe organic solution was washed with saturated NaHCO3 (100 mL) and brine (100 mL)
  4. customColumn purification (hexanes:EtOAc 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-b05d5de93ae146ae84332d77b61aadb1
Quelldatensatz
uspto-grants-2007_06
Patentnummer
USRE039679E1

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