Water → 5-(4-Fluorophenyl)pentan-1-ol

HRID 530496Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530496
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18](O)=[O:19])=[CH:10][CH:9]=1.O.[OH-].[K+]>CCOCC>[F:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:13]=1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14797Potassium HydroxideHCID 27346705-(4-Fluorophenyl)pentanoic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 189717895-(4-Fluorophenyl)pentan-1-olAusbeute 95,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Under nitrogen atmosphere, at 0° C., to a stirring mixture of LiAlH4 (0.46 g, 12.23 mmol) in dry Et2O (5 mL), 5-(4-fluorophenyl)-pentanoic acid (0.6 g, 3.05 mmol) in dry Et2O (35 mL) was added dropwise. The mixture was left to react at rt for 4 h, then at 0° C. H2O (0.46 mL), 3M KOH solution (0.46 mL) and H2O (1.54 mL) were very slowly added. The mixture was stirred for 1 h at 0° C., filtered to remove the solid residue, and the organic phase dried over Na2SO4. The organic solution was again filtered and concentrated to dryness affording the title compound (0.53 g, 95%) as a colorless oil. 1H NMR (CDCl3): δ 1.36-1.47 (m, 2H), 1.58-1.71 (m, 4H), 2.58-2.65 (m, 2H), 3.66 (t, J=5.8 Hz, 2H), 6.94-7.02 (m, 2H), 7.11-7.17 (m, 2H).

Aufarbeitung

  1. additionwas added dropwise
  2. waitThe mixture was left
  3. customto react at rt for 4 h
  4. customat 0° C
  5. filtrationfiltered
  6. customto remove the solid residue
  7. dry with materialthe organic phase dried over Na2SO4
  8. filtrationThe organic solution was again filtered
  9. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-c84494f900b945409f9dc308be74faa7
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353075B2

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