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

HRID 654936Notes

Reaction equation

HRID 654936 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]>C(OCC)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

4

Reactant 1

HCID 109973535-(Pyridin-2-yl)pent-4-yn-1-ol

Product 1

HCID 143474782-Pyridinepentanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

A solution of 5-(2-pyridyl)-4-pentyn-1-ol (1 g, 6.2 mmol) in diethyl ether (15 ml) was hydrogenated over 10% palladium on carbon at room temperature for 16 h. The mixture was filtered through celite and the filtrate on evaporation gave an oil, which was flash chromatographed on silica using 80% ethyl acetate/chloroform. Fractions with Rf of about 0.06 on evaporation gave the title alcohol as a yellow oil.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe filtrate on evaporation
  3. customgave an oil, which
  4. customchromatographed on silica using 80% ethyl acetate/chloroform
  5. customFractions with Rf of about 0.06 on evaporation

Sources & evidence

ORD record
ord-8c36a7b54eb649aeb64e5b8168272bb1
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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