Water → HCID 15477227, compound

HRID 366318Notes

Reaction equation

HRID 366318 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH:11]=[O:12])[O:10][C:6]=2[C:5]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]2=[O:25])=[C:4]([F:26])[CH:3]=1.CC(C)=[O:29].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:13]3[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]3=[O:25])=[C:4]([F:26])[CH:3]=[C:2]([Cl:1])[C:7]=2[CH:8]=1)([OH:29])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 15477226HCID 15477226, compoundHCID 131709961Jones' reagent

Product 1

HCID 15477227HCID 15477227, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.5 g (3.84 mmol) of 3-(4-chloro-6-fluoro-2-formylbenzofuran-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 obtain 1.2 g (yield: 76.9%) of the desired product as white crystals. Melting point: 267-268° C. (decomposed).

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-dcc3bb3c068b43d998df7bf2e3a1fd62
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

Loading…