Tetrahydrofuran → HCID 22221151, compound

HRID 1389015Notes

Reaction equation

HRID 1389015 reaction equation
Cl.NO.[CH2:4]([O:6][C:7](=[O:24])[C:8]([C:13](=[O:23])[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[CH:9][N:10](C)C)[CH3:5].C([O-])(=O)C.[Na+].O1CCCC1>CO>[CH2:4]([O:6][C:7]([C:8]1[CH:9]=[N:10][O:23][C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[O:24])[CH3:5]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 54398161Ethyl 2-(4-nitrobenzoyl)-3-dimethylaminopropenoate

Product 1

HCID 22221151HCID 22221151, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydroxylamine hydrochloride (0.69 g.; 0.01 mol.) was added to a mixture of ethyl-2-(4'-nitrobenzoyl)-3-dimethylaminopropenoate (2.93 g.; 0.01 mol.) and anhydrous sodium acetate (0.82 g.; 0.01 mol.) in 50 ml. of tetrahydrofuran and 25 ml. of methanol. The resultant mixture was stirred at 25° C. for 16 hours until the reaction was complete. The reaction mixture was filtered and the solvent removed from the filtrate by concentration in vacuo. The residue was dissolved in chloroform, extracted with water, dried over magnesium sulfate and then concentrated in vacuo. Recrystallization with ethanol yielded ethyl-5-(4'-nitrophenyl)-4-isoxazolecarboxylate as a white solid (1.2 g.; 45.8% yield) having a melting point of 73°-76° C. and the following analysis:

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent removed from the filtrate by concentration in vacuo
  3. dissolutionThe residue was dissolved in chloroform
  4. extractionextracted with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customRecrystallization with ethanol

Sources & evidence

ORD record
ord-46a6d2f104024b07bf8d6d586b7cf6d3
Source dataset
uspto-grants-1981_01
Patent number
US04243406

Reaction notes

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