6-(Pyridin-3-YL)hex-5-YN-1-OL → 3-Pyridinehexanol

HRID 1583431Notes

Reaction equation

HRID 1583431 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:2]=1>C(O)(C)C.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:2]=1

Participants

4

Reactant 1

HCID 135575516-(Pyridin-3-YL)hex-5-YN-1-OL

Product 1

HCID 36861733-Pyridinehexanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

3-Pyridinehexanol was prepared by hydrogenation of 20.0 g of the crude 6-(3-pyridinyl)-5-hexyn-1-ol, prepared above in Example 105, dissolved in 200 ml of isopropyl alcohol over 2.0 g of 10% palladium on carbon at 1 atmosphere. The crude product obtained after filtration of the catalyst and evaporation of the solvent was evaporatively distilled to yield 15.8 g (89%) of 3-pyridinehexanol as a yellow oil, bp 120°-150° C./0.2 mm which was 90% pure by gas chromatography analysis.

Workup

  1. customprepared above in Example 105
  2. customThe crude product obtained

Sources & evidence

ORD record
ord-02d841415cb24b93871da302c2f07380
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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