(Dimethyl-1,3-thiazol-5-yl)methanol → 2,4-Dimethyl-1,3-thiazole-5-carbaldehyde

HRID 587067Notes

Reaction equation

HRID 587067 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]=1

Participants

4

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

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. filtrationThe mixture was filtered with Celite
  3. washwashed with methanol
  4. customThe solvent was removed under reduced pressure
  5. 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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