2,3-Dihydro-1,4-benzodioxin-5-ol → 1-(diphenylmethyl)-3-hydroxy-3-(5-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1,3-dihydro-2H-indol-2-one

HRID 1407553

Reaktionsgleichung

Reaktionsgleichung von HRID 1407553
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([OH:11])[C:5]=2[O:4][CH2:3][CH2:2]1.C([Mg]Cl)(C)C.[CH:17]([N:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32](=[O:39])[C:31]1=[O:40])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1.ClCCCl>[C:24]1([CH:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:30]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]([OH:39])([C:9]3[CH:8]=[CH:7][C:6]4[O:1][CH2:2][CH2:3][O:4][C:5]=4[C:10]=3[OH:11])[C:31]2=[O:40])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Komponenten

6

Edukt 3

HCID 825202,3-Dihydro-1,4-benzodioxin-5-olHCID 19692771-(diphenylmethyl)-1H-indole-2,3-dioneHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 673581401-(diphenylmethyl)-3-hydroxy-3-(5-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1,3-dihydro-2H-indol-2-oneAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2,3-dihydro-1,4-benzodioxin-5-ol (3.60 g, 23.7 mmol) in anhydrous tetrahydrofuran (80 mL) at 0° C. was added isopropylmagnesium chloride (11.8 mL, 2 M solution in tetrahydrofuran, 23.7 mmol). The mixture was stirred at 0° C. for 45 min, concentrated in vacuo, and 1,2-dichloroethane (60 mL) was added. The mixture was cooled to 0° C. and a solution of 1-benzhydrylindoline-2,3-dione (4.94 g, 15.8 mmol) in 1,2-dichloroethane (70 mL) was added. The reaction mixture was allowed to warm to ambient temperature and stirred for 60 h, and heated to 83° C. and stirred for 3.5 h. The reaction mixture was allowed to cool to ambient temperature, concentrated in vacuo and saturated aqueous ammonium chloride (250 mL) was added. The mixture was extracted with ethyl acetate (250 mL followed by 2×100 mL). The organic phase was washed with water (150 mL) and brine (150 mL), dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was taken up in ethyl acetate and a solid was precipitated by the addition of hexanes to afford 1-(diphenylmethyl)-3-hydroxy-3-(5-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1,3-dihydro-2H-indol-2-one (5.10 g, 69%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ9.14 (s, 1H), 7.43-7.30 (m, 9H), 7.22 (d, J=8.7 Hz, 1H), 6.97-6.79 (m, 3H), 6.52 (s, 1H), 6.44 (d, J=8.7 Hz, 1H) 6.26 (d, J=7.8 Hz, 1H), 4.22 (s, 4H).

Aufarbeitung

  1. concentrationconcentrated in vacuo, and 1,2-dichloroethane (60 mL)
  2. additionwas added
  3. temperatureThe mixture was cooled to 0° C.
  4. temperatureto warm to ambient temperature
  5. stirringstirred for 60 h
  6. temperatureheated to 83° C.
  7. stirringstirred for 3.5 h
  8. temperatureto cool to ambient temperature
  9. concentrationconcentrated in vacuo and saturated aqueous ammonium chloride (250 mL)
  10. additionwas added
  11. extractionThe mixture was extracted with ethyl acetate (250 mL followed by 2×100 mL)
  12. washThe organic phase was washed with water (150 mL) and brine (150 mL)
  13. dry with materialdried over sodium sulfate
  14. filtrationfiltered
  15. concentrationThe filtrate was concentrated in vacuo
  16. customa solid was precipitated by the addition of hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7e8fa355ef354da9a39119141204cfe2
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916580B2

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