Water → HCID 53974449, compound

HRID 863393Notes

Reaction equation

HRID 863393 reaction equation
[CH:1]1([C:4](=[O:26])[C:5](=[CH:22]OCC)[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=2[S:18]([CH3:21])(=[O:20])=[O:19])=[O:7])[CH2:3][CH2:2]1.Cl.[CH2:28]([O:30][NH2:31])[CH3:29].C([O-])(=O)C.[Na+].O>C(O)C>[CH:1]1([C:4](=[O:26])[CH:5]([CH:22]=[N:31][O:30][CH2:28][CH3:29])[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:16])([F:17])[F:15])=[CH:10][C:9]=2[S:18]([CH3:21])(=[O:19])=[O:20])=[O:7])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 76850O-ethylhydroxylamine hydrochlorideHCID 517045Sodium AcetateHCID 53824486HCID 53824486, compound

Product 1

HCID 53974449HCID 53974449, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 3-cyclopropyl-2-ethoxymethylene-1-(2-methylsulphonyl-4-trifluoromethylphenyl)propan-1,3-dione (3.5 g), O-ethylhydroxylamine hydrochloride (0.97 g) and sodium acetate (0.83 g) in ethanol (15 ml) was stirred at 25° C. for 1 hour. The mixture was poured into water and extracted with ethyl acetate. The ethyl acetate solution was dried (anhydrous sodium sulphate) and filtered. The filtrate was evaporated and the residue purified by column chromatography on silica, using a mixture of ethyl acetate and hexane as eluent. The resulting solution was evaporated and 3-cyclopropyl-2-(ethoxyiminomethyl)-1-(2-methylsulphonyl-4-trifluoromethylphenyl)propan-1,3-dione (compound 1) was obtained as white crystals (2 g), m.p. 46° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate solution was dried (anhydrous sodium sulphate)
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customthe residue purified by column chromatography on silica
  6. additiona mixture of ethyl acetate and hexane as eluent
  7. customThe resulting solution was evaporated

Sources & evidence

ORD record
ord-1e927bb9eaa0404d9db99ebf2272b34d
Source dataset
uspto-grants-1998_02
Patent number
US05721193

Reaction notes

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