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

HRID 1375629Notes

Reaction equation

HRID 1375629 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-271a92e480294b68a89c0a9d0bb91ea7
Source dataset
uspto-grants-2007_01
Patent number
US07169798B2

Reaction notes

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