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>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[C:8][CH:9]=[O:10])[CH:2]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-(3-pyridinyl)-2-propynol (500 mg, 3.75 mmol) in CH2Cl2 (5 mL) was treated with activated manganous dioxide (3.3 g, 34.5 mmol) at 25° C. After 12 h, the reaction mixture was filtered through celite, washed with CH2Cl2 (2×50 mL), concentrated in vacuo. Purification by flash chromatography afforded the title compound (100 mg, 20%) as yellow brown oil. MS 133 (M+H)+.
Workup
- filtrationthe reaction mixture was filtered through celite
- washwashed with CH2Cl2 (2×50 mL)
- concentrationconcentrated in vacuo
- customPurification by flash chromatography
Sources & evidence
- ORD record
- ord-aee94fb66d904832999dbb007280ff5f
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06713455B2
Reaction notes
Loading…