Potassium Hydroxide → 5-(4-Fluorophenyl)pentan-1-ol

HRID 1486560Notes

Reaction equation

HRID 1486560 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.[OH-].[K+].N#[N+][O-]>CCOCC.O>[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

7

Reactant 4

HCID 14797Potassium HydroxideHCID 27346705-(4-Fluorophenyl)pentanoic acidHCID 21226445Aluminium lithium hydrideHCID 178514647HCID 178514647, compound

Product 1

HCID 189717895-(4-Fluorophenyl)pentan-1-olYield 97.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

Under nitrogen atmosphere, at 0° C., to a stirring mixture of LiAlH4 (0.27 g, 7.1 mmol) in dry Et2O (6 mL), 5-(4′-fluorophenyl)valeric acid (0.35 g, 1.8 mmol) in dry Et2O (5 mL) was added dropwise. The mixture was left to react at room temperature for 4 hrs, then at 0° C. H2O (0.35 mL), 3M KOH solution (0.35 mL) and N2O (1 mL) were very slowly added. The mixture was stirred for 1 hr 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 (0.32 g, 97%) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 1.34-1.47 (m, 2H), 1.55-1.72 (m, 4H), 2.49-2.68 (m, 2H), 3.64 (t, J=6.56 Hz, 2H), 6.86-7.03 (m, 2H), 7.06-7.17 (m, 2H).

Workup

  1. additionwas added dropwise
  2. waitThe mixture was left
  3. customto react at room temperature for 4 hrs
  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-3b60247cab5a4e0bacc7644e35aa60ec
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

Loading…