3-(Pyridin-2-yl)prop-2-yn-1-ol → Pyripropanol

HRID 654964Notes

Reaction equation

HRID 654964 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]#[C:8][CH2:9][OH:10]>C(OCC)(=O)C.C(O)C.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][CH2:9][OH:10]

Participants

5

Reactant 1

HCID 34811473-(Pyridin-2-yl)prop-2-yn-1-ol

Product 1

HCID 72922Pyripropanol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(2-pyridyl)-2-propyn-1-ol (540 mg, 4.06 mmol) in ethyl acetate (15 ml) and ethanol (3 ml) was hydrogenated over 10% palladium on carbon at room temperature for 13 h. The mixture was filtered through celite and the filtrate on evaporation gave an oil, which was flash chromatographed on silica using 3% methanol/dichloromethane. Fractions with Rf of about 0.09 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 3% methanol/dichloromethane
  5. customFractions with Rf of about 0.09 on evaporation

Sources & evidence

ORD record
ord-70f6016cfde54bb09a2370426e923b5e
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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