Water → 5-(4-Fluorophenyl)pentan-1-ol

HRID 530496Notes

Reaction equation

HRID 530496 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 189717895-(4-Fluorophenyl)pentan-1-olYield 95.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c84494f900b945409f9dc308be74faa7
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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