Sesamol → 3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-7-(trifluoromethyl)-1,3-dihydro-2H-indol-2-one

HRID 1407465

Reaktionsgleichung

Reaktionsgleichung von HRID 1407465
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([OH:10])=[CH:9][C:4]=2[O:3][CH2:2]1.C([Mg]Cl)(C)C.[F:16][C:17]([F:30])([F:29])[C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:26]=1[NH:25][C:24](=[O:27])[C:23]2=[O:28]>O1CCCC1>[OH:28][C:23]1([C:7]2[C:8]([OH:10])=[CH:9][C:4]3[O:3][CH2:2][O:1][C:5]=3[CH:6]=2)[C:22]2[C:26](=[C:18]([C:17]([F:16])([F:29])[F:30])[CH:19]=[CH:20][CH:21]=2)[NH:25][C:24]1=[O:27]

Komponenten

5

Edukt 3

HCID 68289SesamolHCID 6045757-TrifluoromethylisatinHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 673566523-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-7-(trifluoromethyl)-1,3-dihydro-2H-indol-2-oneAusbeute 175 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1,3-benzodioxol-5-ol (9.63 g, 69.7 mmol) in anhydrous tetrahydrofuran (200 mL) was added dropwise a solution of isopropyl magnesium chloride (92.9 mmol, 46.5 mL, 2.0 M solution in tetrahydrofuran) over 30 min at 0° C. 7-Trifluoromethylisatin (4.00 g, 22.0 mmol) was added in one portion. The reaction mixture was stirred at ambient temperature for 4 h and the reaction was quenched by the addition of 10% aqueous hydrochloric acid (25.0 mL) and the mixture was concentrated in vacuo to dryness. The residue was diluted with ethyl acetate (200 mL), washed with saturated ammonium chloride (3×30.0 mL), brine (3×30.0 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was triturated with hot diethyl ether to afford 3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-7-(trifluoromethyl)-1,3-dihydro-2H-indol-2-one (13.6 g, 83%): 1H NMR (300 MHz, DMSO-d6) δ 10.65 (s, 1H), 9.21 (s, 1H), 7.38 (d, J=7.8 Hz, 1H), 7.22 (s, 1H), 7.07 (d, J=7.2 Hz, 1H), 6.95 (dd, J=7.7, 7.7 Hz, 1H), 6.57 (s, 1H), 6.17 (s, 1H), 5.89 (d, J=6.2 Hz, 2H); 13C NMR (75 MHz, DMSO-d6) δ 179.2, 148.6, 147.3, 141.0, 139.9, 135.7, 127.9, 125.3, 124.3, 121.7, 119.8, 110.1, 107.2, 101.2, 97.7, 73.9; MS (ES−) m/z 352.2 (M−1).

Aufarbeitung

  1. customthe reaction was quenched by the addition of 10% aqueous hydrochloric acid (25.0 mL)
  2. concentrationthe mixture was concentrated in vacuo to dryness
  3. additionThe residue was diluted with ethyl acetate (200 mL)
  4. washwashed with saturated ammonium chloride (3×30.0 mL), brine (3×30.0 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo to dryness
  8. customThe residue was triturated with hot diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e119844cb9e04fa184170a1892477162
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916580B2

Verknüpfte Notizen

Wird geladen…