5-(Pyridin-2-yl)pent-4-yn-1-ol → 2-Pyridinepentanol

HRID 2232140Notes

Reaction equation

HRID 2232140 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]#[C:8][CH2:9][CH2:10][CH2:11][OH:12].[H][H]>C(O)C.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12]

Participants

5

Reactant 2

HCID 109973535-(Pyridin-2-yl)pent-4-yn-1-olHCID 178418361HCID 178418361, compound

Product 1

HCID 143474782-PyridinepentanolYield 93.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-(2-Pyridinyl)-4-pentyn-1-ol (8.8 g) was hydrogenated over 1.0 g of 10% Pd/C in 125 mL of ethanol at room temperature and atmospheric pressure. After the uptake of hydrogen had stopped, the catalyst was removed by filtration and the solvent was removed under reduced pressure. The residual oil was distilled on a Kugelrohr apparatus (115°-120° C./0.1 mm) to yield 8.4 g of 2-pyridinepentanol.

Workup

  1. customthe catalyst was removed by filtration
  2. customthe solvent was removed under reduced pressure
  3. distillationThe residual oil was distilled on a Kugelrohr apparatus (115°-120° C./0.1 mm)

Sources & evidence

ORD record
ord-029dc0460e7d425c9c77767598483b35
Source dataset
uspto-grants-1988_11
Patent number
US04786646

Reaction notes

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