Pyridine → HCID 86630047, compound

HRID 2249643Notes

Reaction equation

HRID 2249643 reaction equation
[CH2:1]([O:5][C:6]1[CH:31]=[C:30]([O:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH:29]=[CH:28][C:7]=1[C:8]([C:10]1[CH:11]=[CH:12][C:13]([O:23][CH2:24][CH:25]([CH3:27])[CH3:26])=[C:14]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:15]=1)=O)[CH:2]([CH3:4])[CH3:3].Cl.[NH2:38][OH:39].N1C=CC=CC=1.C(Cl)(Cl)Cl>C(O)C.O>[CH2:1]([O:5][C:6]1[CH:31]=[C:30]([O:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH:29]=[CH:28][C:7]=1[C:8](=[N:38][OH:39])[C:10]1[CH:11]=[CH:12][C:13]([O:23][CH2:24][CH:25]([CH3:27])[CH3:26])=[C:14]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:15]=1)[CH:2]([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6212ChloroformHCID 443297Hydroxyamine hydrochlorideHCID 17816512HCID 17816512, compound

Product 1

HCID 86630047HCID 86630047, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In 20 ml of ethanol is dissolved 10.00 g of ethyl 3-[5-(2,4-diisobutoxybenzoyl)-2-isobutoxyphenyl]-propanoate, to which are added 5.59 g of hydroxylamine hydrochloride and 7 ml of pyridine. The mixture is heated under reflux for 4.5 hours with stirring. After cooling the mixture to ambient temperature, chloroform and water are added, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=5:1) to obtain 10.20 g of ethyl 3-{5-[(2,4-diisobutoxyphenyl)(hydroxyimino)-methyl]-2-isobutoxyphenyl}propanoate as a light brown oily product.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 4.5 hours
  3. customthe organic layer is separated
  4. customThe organic layer thus obtained
  5. washis washed with water and saturated aqueous solution of sodium chloride successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent is distilled off under reduced pressure
  8. customThe residue thus obtained
  9. customis purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-9b7c9d274d214f23a619b3b9330f7e73
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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