Water → HCID 15477224, compound

HRID 366324Notes

Reaction equation

HRID 366324 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH:11]([OH:13])[CH3:12])[O:10][C:6]=2[C:5]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]2=[O:26])=[C:4]([F:27])[CH:3]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.O>CC(C)=O>[C:11]([C:9]1[O:10][C:6]2[C:5]([N:14]3[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]3=[O:26])=[C:4]([F:27])[CH:3]=[C:2]([Cl:1])[C:7]=2[CH:8]=1)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 23289164HCID 23289164, compoundHCID 131709961Jones' reagent

Product 1

HCID 15477224HCID 15477224, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.5 g (3.7 mmol) of 3-[4-chloro-6-fluoro-2-(1-hydroxyethyl) benzofuran-7-yl]-1-methyl-6-trifluoromethyluracil was dissolved in 20 ml of acetone, and a Jones' reagent was dropwise added thereto at 5° C. until the orange color no longer disappeared. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to quantitatively obtain the desired product as pale orange crystals. Melting point: 193-194° C.

Workup

  1. customat 5° C.
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed sequentially with water
  5. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f72b0e6d025d4e0ebc85272a2b519978
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

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