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

HRID 383475

反応式

HRID 383475 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 6-fluorooxindole (2.6 g, 17.5 mmol) in anhydrous THF (30 mL) under nitrogen was added 1.0 M 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%.

後処理

  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

出典と根拠

ORDレコード
ord-b1efd9c2b7b045e18a00bbc540fa478f
出典データセット
uspto-grants-2013_02
特許番号
US08367664B2

関連ノート

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