Trifluoroacetic anhydride → HCID 59479126, compound

HRID 1747026Notes

Reaction equation

HRID 1747026 reaction equation
[C:1]([O:9][CH2:10][C:11]1[CH:12]=[N+:13]([O-])[C:14]([CH3:17])=[CH:15][CH:16]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:22]>CN(C=O)C>[C:1]([O:9][CH2:10][C:11]1[CH:12]=[N:13][C:14]([CH2:17][OH:22])=[CH:15][CH:16]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 59478794HCID 59478794, compound

Product 1

HCID 59479126HCID 59479126, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1891 mg of (6-methyl-1-oxidopyridin-3-yl)methyl benzoate in 38 ml of DMF was added 11 ml of trifluoroacetic anhydride, followed by stirring at room temperature overnight. After evaporating trifluoroacetic anhydride under reduced pressure, a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:chloroform-methanol) to obtain 3.675 g of [6-(hydroxymethyl)pyridin-3-yl]methyl benzoate.

Workup

  1. customAfter evaporating trifluoroacetic anhydride under reduced pressure
  2. additiona saturated aqueous sodium hydrogen carbonate solution was added
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent:chloroform-methanol)

Sources & evidence

ORD record
ord-1cfe30c20ad74fca90533b72912848b9
Source dataset
uspto-grants-2015_10
Patent number
US09150541B2

Reaction notes

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