4-(Pyridin-4-yl)but-3-yn-1-ol → 4-Pyridinebutanol
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]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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).