Dimethylformamide dimethyl acetal → Ethyl 5-(4-bromophenyl)isoxazole-4-carboxylate

HRID 2391107Notes

Reaction equation

HRID 2391107 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])=[CH:4][CH:3]=1.Cl.NO.CO[CH:21](OC)[N:22](C)C>>[CH2:12]([O:11][C:9]([C:8]1[CH:21]=[N:22][O:7][C:6]=1[C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:15][CH:14]=1)=[O:10])[CH3:13]

Participants

4

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 443297Hydroxyamine hydrochlorideHCID 2757149Ethyl 3-(4-bromophenyl)-3-oxopropanoate

Product 1

HCID 22220993Ethyl 5-(4-bromophenyl)isoxazole-4-carboxylate

Conditions

Temperature
100 °C

Procedure

A solution of ethyl (4-bromobenzoyl)acetate (1.19 g, 4.39 mmol) in N,N-dimethylformamide dimethyl acetal (10 mL) was stirred at 100° C. for 1 hour. The mixture was concentrated, and the residue was dissolved in EtOH (10 mL). Hydroxylamine hydrochloride (0.454 g, 6.57 mmol) was added, and the reaction was stirred at 100° C. for 1 hour. After cooling to room temperature, the mixture was partitioned between EtOAc and H2O, and the organic layer was separated, dried over MgSO4, filtered, and concentrated. The crude material was purified by silica gel chromatography to give the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in EtOH (10 mL)
  3. temperatureAfter cooling to room temperature
  4. customthe mixture was partitioned between EtOAc and H2O
  5. customthe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a2118f8352144c2a8a953df5ee426bfe
Source dataset
uspto-grants-2012_09
Patent number
US08273780B2

Reaction notes

Loading…