4-(Pyridin-4-yl)but-3-yn-1-ol → 4-Pyridinebutanol

HRID 1956517Notes

Reaction equation

HRID 1956517 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]#[C:8][CH2:9][CH2:10][OH:11])=[CH:3][CH:2]=1>CO.[Pt](=O)=O>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][CH2:10][OH:11])=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 121814454-(Pyridin-4-yl)but-3-yn-1-ol

Product 1

HCID 27846554-PyridinebutanolYield 83.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

4-(4-Pyridyl)-3-butyn-1-ol (3.5 g) was dissolved in methanol (100 mL) in a Parr hydrogenation bottle and platinum (IV) oxide [Adams' Catalyst] (0.3 g) was added. The Parr bottle was placed on a Parr hydrogenation apparatus and the solution hydrogenated at 40 psi for 2.5 h after which time the starting material had been judged to be consumed by TLC. The spent catalyst was removed by filtration through a Celite pad and the pad carefully washed with more methanol. The combined filtrates were evaporated under reduced pressure on a rotary evaporator and the oily residues then subjected to column chromatography on a short silica column using neat ethyl acetate as the eluant to provide the title compound (3.0 g).

Workup

  1. additionwas added
  2. customto be consumed by TLC
  3. customThe spent catalyst was removed by filtration through a Celite pad
  4. washthe pad carefully washed with more methanol
  5. customThe combined filtrates were evaporated under reduced pressure on a rotary evaporator

Sources & evidence

ORD record
ord-85c43695928649959b1ddcbf66b25a38
Source dataset
uspto-grants-1998_07
Patent number
US05780437

Reaction notes

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