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

HRID 383475

Reaction equation

HRID 383475 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-b1efd9c2b7b045e18a00bbc540fa478f
Source dataset
uspto-grants-2013_02
Patent number
US08367664B2

Linked notes

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