O-ethylhydroxylamine hydrochloride → 2-[1-(Ethoxyimino)propyl]-3-hydroxy-5-[3-methanesulfonamido-2,4,6-trimethylphenyl]cyclohex-2-en-1-one

HRID 477406Notes

Reaction equation

HRID 477406 reaction equation
C([O-])(=O)C.[Na+].Cl.[CH2:7]([O:9][NH2:10])[CH3:8].[C:11]([C:15]1[C:16](=[O:36])[CH2:17][CH:18]([C:22]2[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[C:24]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])[C:23]=2[CH3:35])[CH2:19][C:20]=1[OH:21])(=O)[CH2:12][CH3:13]>C(O)C.C(Cl)Cl>[CH2:7]([O:9][N:10]=[C:11]([C:15]1[C:16](=[O:36])[CH2:17][CH:18]([C:22]2[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[C:24]([NH:30][S:31]([CH3:34])(=[O:32])=[O:33])[C:23]=2[CH3:35])[CH2:19][C:20]=1[OH:21])[CH2:12][CH3:13])[CH3:8]

Participants

6

Reactant 3

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 517045Sodium AcetateHCID 178458846HCID 178458846, compound

Product 1

HCID 1360583542-[1-(Ethoxyimino)propyl]-3-hydroxy-5-[3-methanesulfonamido-2,4,6-trimethylphenyl]cyclohex-2-en-1-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium acetate (0.19 g, 2.29 mmol) and ethoxyamine hydrochloride (0.22 g, 2.29 mmol) were added to a solution of 2-propionyl-3-hydroxy-5-(3-methylsulphonamido-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (0.58 g, 1.53 mmol) in ethanol (25 ml) and methylene chloride (25 ml). Stirring was continued at 20° for 18 hrs. The solvent was removed under reduced pressure and the residue partitioned between chloroform and water. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to yield2-[1-(ethoxyimino)propyl]-hydroxy-5-[3-(methylsulphonamido)-2,4,6-trimethylphenyl]cyclohex-2-en-1-one as a brown oil (0.27 g, 42%). The compound was characterized by proton magnetic resonance spectroscopy. The spectroscopic data are recorded in Table 2.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between chloroform and water
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure to yield2-[1-(ethoxyimino)propyl]-hydroxy-5-[3-(methylsulphonamido)-2,4,6-trimethylphenyl]cyclohex-2-en-1-one as a brown oil (0.27 g, 42%)

Sources & evidence

ORD record
ord-01025e891b464796bd275ba0a3c05ea3
Source dataset
uspto-grants-1989_12
Patent number
US04888043

Reaction notes

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