Trifluoroacetic anhydride → HCID 58478791, compound

HRID 1254084Notes

Reaction equation

HRID 1254084 reaction equation
[CH3:1][C:2]1[N+:7]([O-])=[C:6]2[CH2:9][O:10][C:11](=[O:12])[C:5]2=[CH:4][CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:16]>ClCCl>[OH:16][CH2:1][C:2]1[N:7]=[C:6]2[CH2:9][O:10][C:11](=[O:12])[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 67314368HCID 67314368, compound

Product 1

HCID 58478791HCID 58478791, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-methyl-7H-furo[3,4-b]pyridin-5-one N-oxide (122 mg, 0.74 mmol) in dichloromethane (2 mL) is heated at reflux. Trifluoroacetic anhydride (1.5 mL, 10 mmol) is added dropwise and heating is continued for approximately 30 min. The reaction mixture is cooled and concentrated. The residue is treated with methanol (3 mL) and triethylamine (2 mL) and stirred until no starting material remained. The reaction mixture is concentrated and the residue is purified by chromatography (silica gel). The product containing fractions are concentrated to give the title compound (70 mg, 42%).

Workup

  1. temperatureat reflux
  2. temperatureheating
  3. temperatureThe reaction mixture is cooled
  4. concentrationconcentrated
  5. additionThe residue is treated with methanol (3 mL) and triethylamine (2 mL)
  6. concentrationThe reaction mixture is concentrated
  7. customthe residue is purified by chromatography (silica gel)
  8. additionThe product containing fractions
  9. concentrationare concentrated

Sources & evidence

ORD record
ord-c75cbeaab6d2411988deacb2381c273b
Source dataset
uspto-grants-2013_06
Patent number
US08455535B2

Reaction notes

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