Sodium Chloride → 1-(5-Methyl-3-phenylisoxazol-4-yl)ethanone

HRID 2120852Notes

Reaction equation

HRID 2120852 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].C(N(CC)CC)C.Cl[C:16](=[N:23]O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Na+].[Cl-]>C(O)C.C(OCC)(=O)C>[CH3:5][C:4]1[O:6][N:23]=[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:3]=1[C:2](=[O:7])[CH3:1]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 31261AcetylacetoneHCID 2756315N-hydroxybenzenecarboximidoyl chloride

Product 1

HCID 3185241-(5-Methyl-3-phenylisoxazol-4-yl)ethanoneYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of pentane-2,4-dione (13.23 g, 0.132 mol) and triethylamine (13.35 g, 0.132 mol) in ethanol was added α-chlorobenzaldehyde oxime (13.70 g, 0.088 mol) at room temperature. The reaction mixture was stirred overnight at room temperature. To the reaction was added ethyl acetate and saturated aqueous NaCl. The organic phase was washed with saturated aqueous NaCl (twice) and dried with MgSO4, and the organic solvent was removed under reduced pressure to provide 17.7 g of the title compound. The yield was 100%.

Workup

  1. washThe organic phase was washed with saturated aqueous NaCl (twice) and
  2. dry with materialdried with MgSO4
  3. customthe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-189fbd872f3846ebb96b2d9c288bef26
Source dataset
uspto-grants-2004_02
Patent number
US06693108B2

Reaction notes

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