Dimethylformamide dimethyl acetal → Ethyl 5-(4-bromophenyl)isoxazole-4-carboxylate
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
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
- concentrationThe mixture was concentrated
- dissolutionthe residue was dissolved in EtOH (10 mL)
- temperatureAfter cooling to room temperature
- customthe mixture was partitioned between EtOAc and H2O
- customthe organic layer was separated
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude material was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-07a74435cf6548f7a5f638841f2ec1f3
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08058300B2
Reaction notes
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