Water → HCID 178468719, compound

HRID 70504Notes

Reaction equation

HRID 70504 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=[O:4].[CH:14]1([C:17]2[CH:22]=[N+:21]([O-])[C:20]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:19][CH:18]=2)[CH2:16][CH2:15]1.O>CN(C)C=O>[CH:14]1([C:17]2[CH:18]=[CH:19][C:20]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[N:21][C:22]=2[OH:4])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 67396289HCID 67396289, compound

Product 1

HCID 178468719HCID 178468719, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Trifluoroacetic anhydride (23 mL) was added to a solution of ethyl 5-cyclopropylpyridine-2-carboxylate 1-oxide (15.4 g) in N,N-dimethylformamide (45 mL), and the mixture was stirred at 50° C. for two hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1) to give ethyl 5-cyclopropyl-6-hydroxypyridine-2-carboxylate (12.4 g, 78%) as a colorless powder.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1)

Sources & evidence

ORD record
ord-c9a133412cf741ff87f0d68c0321cf23
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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