Water → HCID 15457194, compound

HRID 1385950Notes

Reaction equation

HRID 1385950 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][C:8]([CH:11]=[O:12])=[CH:7][C:6]=2[C:5]([C:13]2[C:14](=[O:24])[N:15]([CH3:23])[C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=2)=[C:4]([F:25])[CH:3]=1.CC(C)=[O:28].OS(O)(=O)=O.O=[Cr](=O)=O.O>CC(C)=O>[C:11]([C:8]1[O:9][C:10]2[C:2]([Cl:1])=[CH:3][C:4]([F:25])=[C:5]([C:13]3[C:14](=[O:24])[N:15]([CH3:23])[C:16]([C:19]([F:20])([F:22])[F:21])=[CH:17][CH:18]=3)[C:6]=2[CH:7]=1)([OH:28])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 15457193HCID 15457193, compoundHCID 131709961Jones' reagent

Product 1

HCID 15457194HCID 15457194, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
-20 °C

Procedure

0.37 g (0.99 mmol) of 3-(7-chloro-5-fluoro-2-formylbenzofuran-4-yl)-1-methyl-6-trifluoromethyl-2-(1H)-pyridone was dissolved in 20 ml of acetone, and a Jones reagent (CrO3—H2SO4) was added thereto at −20° C. After stirring at −20° C. for 2 hours, the mixture was poured into water and extracted with ethyl acetate. An aqueous sodium hydroxide solution was added to make the extract alkaline, and the aqueous layer was washed with ethyl acetate and acidified by an addition of hydrochloric acid and then extracted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. Then, the obtained crude crystals were washed with diisopropyl ether to obtain 0.29 g (yield: 75%) of the desired products Melting point: 233-235° C. 1H-NMR (300 MHz, CDCl3) δ value: 3.79(3H,s), 6.87(1H,d), 7.38(1H,d), 7.47(1H,s), 7.61(1H,d)ppm.

Workup

  1. customat −20° C
  2. extractionextracted with ethyl acetate
  3. additionAn aqueous sodium hydroxide solution was added
  4. washthe aqueous layer was washed with ethyl acetate
  5. additionacidified by an addition of hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. washAfter washing with water
  8. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  9. distillationEthyl acetate was distilled off under reduced pressure
  10. customThen, the obtained crude crystals
  11. washwere washed with diisopropyl ether

Sources & evidence

ORD record
ord-fcfc171f9ad74ef6bb01263d6ce29e1b
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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