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

HRID 557682ノート

反応式

HRID 557682 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

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

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-07a74435cf6548f7a5f638841f2ec1f3
出典データセット
uspto-grants-2011_11
特許番号
US08058300B2

反応ノート

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