Trifluoroacetic acid → HCID 53680539, compound

HRID 861328Notes

Reaction equation

HRID 861328 reaction equation
[CH3:1][C:2]1[N+:7]([O-])=[C:6]([C:9]([O:11][CH3:12])=[O:10])[C:5]([C:13]([C:15]2[CH:20]=[CH:19][C:18]3[O:21][CH2:22][O:23][C:17]=3[CH:16]=2)=[O:14])=[CH:4][CH:3]=1.FC(F)(F)C(O)=[O:27]>CN(C=O)C>[CH3:12][O:11][C:9]([C:6]1[C:5]([C:13]([C:15]2[CH:20]=[CH:19][C:18]3[O:21][CH2:22][O:23][C:17]=3[CH:16]=2)=[O:14])=[CH:4][CH:3]=[C:2]([CH2:1][OH:27])[N:7]=1)=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54197406HCID 54197406, compound

Product 1

HCID 53680539HCID 53680539, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF(15 ml) solution of 6-methyl-3-(3,4-methylenedioxyphenylcarbonyl)-2-methoxycarbonylpyridine N-oxide(1.56 g,4.95 mmol) was added anhydrous trifluoro acetic acid(7 ml) under ice-cooling, and the mixture was stirred at room temperature for 18 h. After removal of the excess anhydrous trifluoro acetic acid the residue was partitioned between water and AcOEt. The organic layer was washed with a saturated aqueous solution of NaHCO3 and brine, dried over MgSO4 and concentrated under reduced pressure to give 6-hydroxymethyl-3-(3,4-methylenedioxyphenylcarbonyl)pyridine-2-carboxylic acid methyl ester(1.72 g).

Workup

  1. temperaturecooling
  2. customAfter removal of the excess anhydrous trifluoro acetic acid the residue
  3. customwas partitioned between water and AcOEt
  4. washThe organic layer was washed with a saturated aqueous solution of NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-da3c7cd973c1462ea5eedde50b9184cf
Source dataset
uspto-grants-1998_02
Patent number
US05714479

Reaction notes

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