Sodium Hydroxide → 5-(m-Tolyl)isoxazole

HRID 2254449Notes

Reaction equation

HRID 2254449 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][CH:10]=[N:11][OH:12])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>C(O)C.Cl>[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86662876N-hydroxy-3-(3-methylphenyl)prop-2-yn-1-imine

Product 1

HCID 197446775-(m-Tolyl)isoxazoleYield 87%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

122 mg of the resulting oxime compound was dissolved in 20 ml of ethanol, and one drop of a 1N aqueous solution of sodium hydroxide was added. The solution was left to stand for 3 minutes, and three drops of 1N HCl was added to terminate the reaction. The solvent was evaporated under reduced pressure. The residue was extracted with a mixture of water and ethyl ether. The organic layer was separated, and the solvent was evaporated to give 106 mg (yield 87%) of the captioned compound as a pale yellow oil.

Workup

  1. waitThe solution was left
  2. customto terminate
  3. customthe reaction
  4. customThe solvent was evaporated under reduced pressure
  5. extractionThe residue was extracted with a mixture of water and ethyl ether
  6. customThe organic layer was separated
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-124aa7d7cb334362a57802c07044c6fd
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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