(+-)-3-Methyl-2,4(3H,5H)-furandione → 6-fluoro-3-(4-methoxy-5H-furan-2-ylidene)-1,3-dihydro-indol-2-one

HRID 333355

반응식

HRID 333355 반응식
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:22]1[CH2:26][O:25][CH2:24][CH2:23]1.CC1C(=O)OC[C:29]1=[O:30]>C1COCC1>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[C:24]3[CH:23]=[C:22]([O:30][CH3:29])[CH2:26][O:25]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 544553(+-)-3-Methyl-2,4(3H,5H)-furandioneHCID 37310136-fluoro-2,3-dihydro-1H-indol-2-oneHCID 23714775LiHMDS tetrahydrofuran

생성물 1

HCID 694016066-fluoro-3-(4-methoxy-5H-furan-2-ylidene)-1,3-dihydro-indol-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 6-fluorooxindole (2.6 g, 17.5 mmol) in anhydrous THF (30 mL) under nitrogen was added 1.0M LiHMDS/THF solution (35 mL, 35 mmol). The mixture was stirred at room temperature for 10 minutes. Methyl tetronate (1.0 g, 8.8 mmol) was added as one portion. After stirring at room temperature for 1 hour, the reaction was cooled to 0° C., and quenched with 2M HCl until pH=3. The mixture was stirred at room temperature for 2 more hours, and poured into 250 mL of water. The resulting precipitates were filtered, rinsed with water and dried in vacuum to give 6-fluoro-3-(4-methoxy-5H-furan-2-ylidene)-1,3-dihydro-indol-2-one as off-white solid. Yield: 840 mg, 38%.

후처리

  1. stirringAfter stirring at room temperature for 1 hour
  2. temperaturethe reaction was cooled to 0° C.
  3. customquenched with 2M HCl until pH=3
  4. stirringThe mixture was stirred at room temperature for 2 more hours
  5. additionpoured into 250 mL of water
  6. customThe resulting precipitates
  7. filtrationwere filtered
  8. washrinsed with water
  9. customdried in vacuum

출처 및 근거

ORD 기록
ord-63bc797482c34a3ca866297acc8a62d6
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877923B2

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