Water → HCID 54057436, compound

HRID 2256902Notes

Reaction equation

HRID 2256902 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[C:14]1[O:18][N:17]=[CH:16][CH:15]=1)([O-:3])=[O:2].[O-]CC.[Na+].O>C(O)C>[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=[CH:6][C:5]=1[C:14](=[O:18])[CH2:15][C:16]#[N:17])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 2723922Sodium ethoxideHCID 53802621HCID 53802621, compound

Product 1

HCID 54057436HCID 54057436, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 5-(2-nitro-4-trifluoromethylphenyl)-isoxazole (4.91 g) in ethanol (35 ml) was added dropwise to a solution of sodium ethoxide in ethanol (prepared from 0.6 g sodium in 25 ml ethanol). The mixture was stirred at room temperature for 3 hours, poured into water (150 ml) and acidified to pH 1. It was extracted with ether (2×75 ml) and the combined extracts were washed with water, dried (anhydrous sodium sulphate) and filtered. The filtrate was evaporated to dryness and the residue was triturated with petroleum spirit (bp 60°-80° C.) and filtered to give 3-(2-nitro-4-trifluoromethylphenyl)-3-oxopropionitrile (4.9 g) as an off-white solid mp 79.5°-80.5° C.

Workup

  1. extractionIt was extracted with ether (2×75 ml)
  2. washthe combined extracts were washed with water
  3. dry with materialdried (anhydrous sodium sulphate)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was triturated with petroleum spirit (bp 60°-80° C.)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-cb8002765e644e3eb6772c60c6f592f0
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

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