Trifluoroacetic anhydride → HCID 10702393, compound

HRID 376279Notes

Reaction equation

HRID 376279 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N+:7]=1[O-].FC(F)(F)C(OC(=O)C(F)(F)F)=[O:17].[OH-].[Na+]>O1CCCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([CH2:12][OH:17])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 19361778HCID 19361778, compound

Product 1

HCID 10702393HCID 10702393, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2.75 g of 2-furan-2-yl-6-methylpyridine 1-oxide (15.7 mmol) are dissolved in 27 ml of tetrahydrofuran. 6.65 ml of trifluoroacetic anhydride (47.1 mmol) are added to the solution cooled to 0° C. under a nitrogen atmosphere. The mixture is stirred for 12 hours at room temperature and then 25 ml of a 4N aqueous solution of sodium hydroxide are added. The tetrahydrofuran is evaporated off, the residue is taken up in a saturated aqueous solution of sodium chloride and then the mixture is extracted with chloroform. The organic phase is dried over magnesium sulfate, filtered and concentrated under vacuum. The title product is isolated by chromatography on a silica column (eluent: chloroform/ethyl acetate; 90:10). 2.03 g of a yellow oil are recovered.

Workup

  1. customThe tetrahydrofuran is evaporated off
  2. extractionthe mixture is extracted with chloroform
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-73b47bfd12f1413a9324d426baac0150
Source dataset
uspto-grants-2000_02
Patent number
US06020345

Reaction notes

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