Trifluoroacetic anhydride → (4,6-Dimethylpyridin-2-yl)methanol

HRID 1910753Notes

Reaction equation

HRID 1910753 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N+:3]=1[O-].FC(F)(F)C(OC(=O)C(F)(F)F)=[O:14]>>[CH3:8][C:6]1[CH:7]=[C:2]([CH3:1])[N:3]=[C:4]([CH2:9][OH:14])[CH:5]=1

Participants

3

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 76904Pyridine, 2,4,6-trimethyl-, 1-oxide

Product 1

HCID 4296719(4,6-Dimethylpyridin-2-yl)methanolYield 50%

Procedure

Trifluoroacetic anhydride (20 mL) was added to 2,4,6-trimethyl-pyridine-1-oxide (2.0 g, 14.6 mmol) at 0° C., then the mixture was stirred at room temperature for 5 h. The mixture was concentrated in vacuo, diluted with water and extracted with ethyl acetate. The organic phase was washed with water, dried over anhydrous sodium sulfate and concentrated to afford a residue which was purified by column chromatography on silica gel (60-120 mesh), eluting with 25% ethyl acetate/hexane, to afford (4,6-dimethyl-pyridin-2-yl)-methanol (1.0 g, 50%)-s a dark brown liquid

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto afford a residue which
  8. customwas purified by column chromatography on silica gel (60-120 mesh)
  9. washeluting with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-94cf8da2a0034d9cae4e29d2dab8a96e
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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