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

HRID 852079노트

반응식

HRID 852079 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d23042a69e9341eaacf5cf25b1c49686
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253165B2

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