3-(3-Pyridyl)-2-propyn-1-ol → 3-(3-Pyridinyl)-2-propynal
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[C:8][CH2:9][OH:10])[CH:2]=1>C(Cl)Cl.O=[Mn]=O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[C:8][CH:9]=[O:10])[CH:2]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 3-(3-pyridinyl)-2-propyn-1-ol (250 mg, 1.88 mmol, obtained as described in J. Org Chem. 1998, 63, 1109-1118) in anhydrous DCM (10 ml) under argon was added MnO2 (3.66 g, 42 mmol) portion wise over 1.5 h. The reaction mixture was stirred at rt for one additional hour. Then the reaction mixture was poured on the top of a column of silica gel and eluted with cHex/EtOAc (2:1 then 1:1) to give 43 mg (17%) of the title compound as a yellow powder. 1H NMR (CDCl3) δ: 9.46 (s, 1H), 8.85 (dd, J=2.1, 0.8 Hz, 1H), 8.71 (dd, J=5.0, 1.7 Hz, 1H), 7.91 (ddd, J=8.0, 2.1, 1.7 Hz, 1H), 7.38 (ddd, J=8.0, 5.0, 0.8 Hz, 1H).