Magnesium perchlorate → 2-Hydroxy-3-(4-methoxyindolin-1-yl)-3-phenylpropanol

HRID 1279493

Reaktionsgleichung

Reaktionsgleichung von HRID 1279493
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][NH:7]2.Cl([O-])(=O)(=O)=O.[Mg+2].Cl([O-])(=O)(=O)=O.[O:23]1[CH:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]1[CH2:25][OH:26]>CC#N.C([O-])(O)=O.[Na+]>[OH:23][CH:24]([CH:27]([N:7]1[C:8]2[C:4](=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][CH:9]=2)[CH2:5][CH2:6]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:25][OH:26]

Komponenten

6

Edukt 3

HCID 24840Magnesium perchlorateHCID 89553(3-Phenyloxiranyl)methanolHCID 162444414-methoxy-2,3-dihydro-1H-indole

Produkt 1

HCID 184284162-Hydroxy-3-(4-methoxyindolin-1-yl)-3-phenylpropanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittel2×HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A solution of 1.00 g (6.62 mmol) of 4-methoxyindoline (Gangjee et al., J. Med. Chem. 1997, 40, 479-485) and 1.90 g (8.51 mmol) of magnesium perchlorate in 20 mL of CH3CN was treated in a dropwise manner with a solution of 1.00 g (6.62 mmol) of 2,3-epoxy-3-phenyl-1-propanol (Ogata and Tomizawa, Bull. Chim. Soc. Jap. 1977, 50, 261-265) in 10 mL of CH3CN. The reaction was stirred at ambient temperature for 2.5 hours and was diluted with 30 mL of saturated aqueous NaHCO3. The organic layer was separated and the aqueous phase was extracted with EtOAc (2×20 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The oil was purified by radial chromatography (SiO2; 10% then 20% then 30% EtOAc in hexanes) to afford 1.55 g (5.17 mmol; 78%) of the subtitled compound as a solid.

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous phase was extracted with EtOAc (2×20 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe oil was purified by radial chromatography (SiO2

Quellen und Nachweise

ORD-Eintrag
ord-fba1dbd9606b4768b5f2bb98b07bc2bb
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06448284B1

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