Water → HCID 22735140, compound

HRID 2392993Notes

Reaction equation

HRID 2392993 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:9]=[N:10][O:11][C:12]=2[CH:13]2[CH2:15][CH2:14]2)=[O:7])=[C:4]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:3]=1.[O-]CC.[Na+].O>C(O)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6](=[O:7])[CH:8]([C:9]#[N:10])[C:12]([CH:13]2[CH2:15][CH2:14]2)=[O:11])=[C:4]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2723922Sodium ethoxideHCID 15452203Isoxachlortole

Product 1

HCID 22735140HCID 22735140, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A suspension of 4-[4-chloro-2-(methylsulphonyl)benzoyl]-5-cyclopropylisoxazole (2.2 g) in ethanol was added to a solution of sodium ethoxide in ethanol (prepared from sodium (0.2 g) and ethanol). The mixture was stirred at room temperature for 2 hours then poured into water and acidified to pH 1. It was extracted with ethyl acetate, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was recrystallised from ethyl acetate and cyclohexane to give 1-[4-chloro-2-(methylsulphonyl)phenyl]-2-cyano-3-cyclopropylpropan-1,3-dione, COMPOUND 612, (1.7 g) as a light brown solid, m.p. 116° C.

Workup

  1. extractionIt was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was recrystallised from ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-b51d3f1405c04153bb25b60b6191631c
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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