(Dimethyl-1,3-thiazol-5-yl)methanol → 2,4-Dimethyl-1,3-thiazole-5-carbaldehyde
Reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH2:8][OH:9])=[C:5]([CH3:7])[N:6]=1>C1COCC1.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[S:3][C:4]([CH:8]=[O:9])=[C:5]([CH3:7])[N:6]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
In THF (20 ml) was dissolved (2,4-dimethyl-1,3-thiazol-5-yl)methanol (1.0 g). To the solution was added active manganese dioxide (6.0 g), and the mixture was stirred at room temperature for 3 hours. To the mixture was added active manganese dioxide (3.0 g), and the mixture was stirred at room temperature for 1 hour. The mixture was filtered with Celite and washed with methanol. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate/methanol=10/10/1) to give 2,4-dimethyl-1,3-thiazole-5-carbaldehyde (0.32 g).
Workup
- stirringthe mixture was stirred at room temperature for 1 hour
- filtrationThe mixture was filtered with Celite
- washwashed with methanol
- customThe solvent was removed under reduced pressure
- customthe resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate/methanol=10/10/1)
Sources & evidence
- ORD record
- ord-bae70c39265a4155985234f3c929fffd
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06936602B1
Reaction notes
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