Water → HCID 178431795, compound

HRID 1096806Notes

Reaction equation

HRID 1096806 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3](=[O:10])[CH:4]([CH3:9])[C:5]([NH:7]O)=[O:6].O>OS(O)(=O)=O>[CH3:9][C:4]1[C:5]([OH:6])=[N:7][O:10][C:3]=1[C:2]([F:12])([F:11])[F:1]

Participants

4

Reactant 2

HCID 962WaterHCID 100811044,4,4-Trifluoro-N-hydroxy-2-methyl-3-oxobutyramide

Product 1

HCID 178431795HCID 178431795, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
75 °C

Procedure

4,4,4-Trifluoro-N-hydroxy-2-methyl-3-oxobutyramide (500 mg, 2.70 mmol) was dissolved in aq. 90% H2SO4 (5.5 mL). The mixture was heated to 75° C. for 90 min, and then allowed to cool to rt. Water (15 mL) was added, and the mixture was extracted with Et2O (2×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification by FC (EtOAc/heptane/AcOH 20:80:1→25:75:1→33:66:1) yielded the title compound (197 mg, 44%). TLC: Rf=0.43 (EtOAc/heptane 1:1+1% AcOH).

Workup

  1. temperatureto cool to rt
  2. extractionthe mixture was extracted with Et2O (2×)
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification by FC (EtOAc/heptane/AcOH 20:80:1→25:75:1→33:66:1)

Sources & evidence

ORD record
ord-1109117c8e5043e08b87392eb89d2e6f
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

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