HCID 22734448, compound → HCID 22734278, compound

HRID 2084792Notes

Reaction equation

HRID 2084792 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:23])[C:7]=1[CH2:8][CH:9]([C:11]1[C:20]2[O:19][CH2:18][CH2:17][O:16][C:15]=2[C:14]([O:21][CH3:22])=[CH:13][CH:12]=1)[OH:10].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:23])[C:7]=1[CH2:8][C:9]([C:11]1[C:20]2[O:19][CH2:18][CH2:17][O:16][C:15]=2[C:14]([O:21][CH3:22])=[CH:13][CH:12]=1)=[O:10]

Participants

4

Reactant 2

HCID 22734448HCID 22734448, compoundHCID 131709961Jones' reagent

Product 1

HCID 22734278HCID 22734278, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Compound 178a (3.0 g) obtained in Step A was dissolved in acetone (30 ml), mixed with Jones reagent (2.6 M) (4.9 ml), and stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure. The resulting residue was mixed with water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate anhydride, and evaporated under reduced pressure for removing the solvent. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to give Compound 178 (3.0 g, 75%) as colorless crystals.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionThe resulting residue was mixed with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate anhydride
  6. customevaporated under reduced pressure
  7. customfor removing the solvent
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-26e2acd0a1a94d35a18918df7fb519f5
Source dataset
uspto-grants-2004_04
Patent number
US06716987B1

Reaction notes

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