Methanol → 3-PYRIDINEPENTANOL

HRID 1463368Notes

Reaction equation

HRID 1463368 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH:8](O)[CH2:9][C:10]#[CH:11])[CH:2]=1.[H][H].C[OH:16]>[Pd].C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:16])[CH:2]=1

Participants

6

Reactant 3

HCID 887Methanol2×HCID 19090131HCID 19090131, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 6428103-PYRIDINEPENTANOLYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-(3-Pyridyl)-1-pentyn-4-ol (0.776 g, 4.82 mmol) was added to a stirred suspension of 10% palladium on charcoal (0.2 g) in methanol (30 ml). The reaction was stirred at room temperature under a hydrogen atmosphere for 48 h, by which time hydrogen uptake had ceased. The mixture was filtered through celite and evaporated to provide a yellow oil. Column chromatography (flash silica gel, 5% methanol in ethyl acetate) gave 5-(3-pyridyl)-1-pentanol (0.769 g, 97%) as a colourless oil.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customevaporated
  3. customto provide a yellow oil

Sources & evidence

ORD record
ord-64db3618023c49aab90da2aa2b806eb2
Source dataset
uspto-grants-1994_04
Patent number
US05300524

Reaction notes

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