Water → 6-Fluoro-3-(3-methoxy-phenyl)-benzo[d]isoxazole

HRID 852079ノート

反応式

HRID 852079 の反応式
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)=[N:10][OH:11].CC(C)([O-])C.[K+].C(OCC)(=O)C.O>O1CCCC1>[F:8][C:6]1[CH:5]=[CH:4][C:3]2[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)=[N:10][O:11][C:2]=2[CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 72465824(2,4-Difluoro-phenyl)-(3-methoxy-phenyl)-methanone oxime

生成物 1

HCID 179062626-Fluoro-3-(3-methoxy-phenyl)-benzo[d]isoxazole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Cool (2,4-difluoro-phenyl)-(3-methoxy-phenyl)-methanone oxime (52.66 g, 217 mmol) in tetrahydrofuran (500 mL) to 0° C. Add 1.0 M solution of potassium tert-butoxide in tetrahydrofuran (260 mL, 0.26 mol) and stir at room temperature for 1.5 hours. Reflux reaction mixture for an additional 1.5 hours. Cool to room temperature overnight. Dilute reaction mixture with ethyl acetate and water and separate. Dry the organic layer and concentrate to give the title compound as an oil. Purify by column chromatography (dichloromethane) and triturate with pentane to give the title compound as a white solid (30.2 g, 62% Yield). NMR and M/S are consistent with the final, desired compound. mp=68-69° C.

後処理

  1. temperatureReflux
  2. customreaction mixture for an additional 1.5 hours
  3. temperatureCool to room temperature overnight
  4. additionDilute
  5. customseparate
  6. customDry the organic layer
  7. concentrationconcentrate

出典と根拠

ORDレコード
ord-d23042a69e9341eaacf5cf25b1c49686
出典データセット
uspto-grants-2007_08
特許番号
US07253165B2

反応ノート

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