(3-Methylpyridin-2-yl)methanol → 3-Methylpyridine-2-carboxaldehyde
Reaction equation
[OH:1][CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N:4]=1>C(Cl)Cl.O=[Mn]=O>[CH3:9][C:8]1[C:3]([CH:2]=[O:1])=[N:4][CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of 2-(hydroxymethyl)-3-methylpyridine (1.08 g, 8.77 mmol) in dry CH2Cl2 (45 mL) at room temperature was added MnO2 (8.09 g, 79.1 mmol). The mixture was stirred for 21 hrs then filtered through celite. The filtrate was concentrated to give 0.68 g (64%) of 3-methylpyridine-2-carboxaldehyde. 1H NMR (CDCl3) □ 2.66 (s, 3H), 7.39 (dd, 1H, J=8.3, 4.3 Hz), 7.63 (d, 1H, J=7.9 Hz), 8.66 (d, 1H, J=3.3 Hz), 10.19 (s, 1H). This was used without further purification.
Workup
- filtrationthen filtered through celite
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-9b276c372b2c47e7b5b6464e07e242b6
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07084155B2
Reaction notes
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