Acetic Anhydride → [4-(Trifluoromethyl)pyridin-2-yl]methyl acetate

HRID 2367050Notes

Reaction equation

HRID 2367050 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N+:3]=1[O-].[C:13]([O:16]C(=O)C)(=[O:15])[CH3:14].C([O-])(O)=O.[Na+]>C(O)C>[C:13]([O:16][CH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 147614494-Trifluoromethyl-2-picoline-N-oxide

Product 1

HCID 14761451[4-(Trifluoromethyl)pyridin-2-yl]methyl acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methyl-4-(trifluoromethyl)pyridine 1-oxide (4.0 g, 22 mmol) was added to acetic anhydride (12 mL) at 120° C. The mixture was refluxed for 1 h. To it was carefully added 10 mL of ethanol. Reflux was continued for 10 min. The mixture was poured into ice, neutralized with NaHCO3, and extracted with Et2O. The organic layer was dried (MgSO4) and concentrated. Chromatography on silica gel (5:2 hexanes/EtOAc) provided the product (3.4 g) as a brown oil. MS (M+H) 220.1.

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. temperatureReflux
  3. additionThe mixture was poured into ice
  4. extractionextracted with Et2O
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f660664ddd1e4a429f1e2e674aa0422d
Source dataset
uspto-grants-2014_04
Patent number
US08697870B2

Reaction notes

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