Trifluoroacetic anhydride → HCID 67272592, compound

HRID 250947Notes

Reaction equation

HRID 250947 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N+:3]=1[O-].[C:14](OC(C(F)(F)F)=O)(C(F)(F)F)=[O:15].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.[Cl-].[Na+].O>[CH3:1][C:2]1([CH2:14][OH:15])[C:7]([CH3:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][NH:3]1

Participants

6

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 11430Potassium CarbonateHCID 67272534HCID 67272534, compound

Product 1

HCID 67272592HCID 67272592, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2,3-dimethyl-5-trifluoromethyl-pyridine 1-oxide (0.620 g, 3.24 mmol) in CH2Cl2 (20 mL) was added TFAA (1.36 g, 6.48 mmol) at room temperature. After the mixture was stirred at room temperature for 3 h, brine (5 mL) and K2CO3 (20 mL) were added. The mixture was stirred at room temperature for 1 h and then extracted with CH2Cl2 (3×20 mL). The extracts were combined and dried over Na2SO4. After filtration the solvent was removed, and the residue was purified on silica gel column (4:1, CH2Cl2/Et2O), affording (2,3-dimethyl-5-trifluoromethyl-pyridin-2-yl)-methanol as a pale yellow oil (0.300 g, 48%).

Workup

  1. stirringThe mixture was stirred at room temperature for 1 h
  2. extractionextracted with CH2Cl2 (3×20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration the solvent
  5. customwas removed
  6. customthe residue was purified on silica gel column (4:1, CH2Cl2/Et2O)

Sources & evidence

ORD record
ord-d76d13dd5c514e2b9040bae863d406bd
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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