Water → ethyl hydroxy-(1-methyl-2-phenyl-1H-indol-3-yl)-acetate

HRID 590978

Reaktionsgleichung

Reaktionsgleichung von HRID 590978
[BH4-].[BH4-].[BH4-].[BH4-].[Na+].[Na+].[Na+].[Na+].[CH3:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19](=[O:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:11]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>O1CCCC1.CO>[OH:25][CH:19]([C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:10]([CH3:9])[C:11]=1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Komponenten

6

Edukt 3

HCID 962WaterHCID 70855253ethyl (1-methyl-2-phenyl-1H-indol-3-yl)-oxo-acetateHCID 131720822Sodium tetraborohydride

Produkt 1

HCID 70855247ethyl hydroxy-(1-methyl-2-phenyl-1H-indol-3-yl)-acetateAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

At 0° C., sodium tetraborohydride (78 mg, 2 mmol) was added to a solution of ethyl (1-methyl-2-phenyl-1H-indol-3-yl)-oxo-acetate (8a) (630 mg, 2.05 mmol) in a mixture of tetrahydrofuran (10 mL) and methanol (15 mL). The mixture was stirred at room temperature for 2 hours and then hydrolyzed with water. Methanol and tetrahydrofuran were removed under reduced pressure and the residue was diluted with dichloromethane. The organic layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (dichloromethane) to afford the desired alcohol (8b) (440 mg, 1.42 mmol, 69%).

Aufarbeitung

  1. customMethanol and tetrahydrofuran were removed under reduced pressure
  2. additionthe residue was diluted with dichloromethane
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-28973bfa09cd4955b5bf124020eadc92
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238026B2

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