Hydroxyamine hydrochloride → Ethyl 5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylate

HRID 1510436Notes

Reaction equation

HRID 1510436 reaction equation
O=[C:2]([CH2:8][C:9](=[O:20])[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].Cl.[NH2:22]O>C(O)C>[F:17][C:16]([F:19])([F:18])[C:13]1[CH:14]=[CH:15][C:10]([C:9]2[O:20][N:22]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:8]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 611940Ethyl 2,4-dioxo-4-[4-(trifluoromethyl)phenyl]butanoate

Product 1

HCID 22064085Ethyl 5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylateYield 65.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2,4-dioxo-4-(4-(trifluoromethyl)phenyl)butanoate (6.89 g, 23.9 mmol) and hydroxylamine hydrochloride (2.0 g, 28.7 mmol) in ethanol (120 mL) was stirred at reflux overnight. The volatiles were removed in vacuo, and the residue purified by silica gel chromatography, eluting with dichloromethane to obtain the title compound (4.5 g, 15.6 mmol).

Workup

  1. temperatureat reflux overnight
  2. customThe volatiles were removed in vacuo
  3. customthe residue purified by silica gel chromatography
  4. washeluting with dichloromethane

Sources & evidence

ORD record
ord-855b5b9f7a724f8399e71d0c897e83c5
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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