Water → (1H-indol-2-yl)methanol

HRID 25159

Reaktionsgleichung

Reaktionsgleichung von HRID 25159
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]1[C:16](OCC)=[O:17].O.[OH-].[Na+]>C1COCC1>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]1[CH2:16][OH:17]

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 73125Ethyl indole-2-carboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 98783(1H-indol-2-yl)methanolAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of lithium aluminum hydride (10.6 g, 264 mmol) in THF (200 mL) is added dropwise a solution of ethyl indole-2-carboxylate (50.0 g, 256 mmol) in THF (250 mL) over 25 minutes. After 3 h, water (10.6 mL) is carefully added, followed by 15% NaOH (10.6 mL), followed by additional portion of water (31.8 mL). The resulting suspension is dried (Na2SO4) and filtered through celite. After concentration under reduced pressure, the white solid (34.0 g) is crystallized from EtOAc/hexanes to give white needles for 1H-indol-2-ylmethanol. Yield 83%. HRMS (FAB) calcd for C9H9NO+H 148.0762, found 148.0771.

Aufarbeitung

  1. dry with materialThe resulting suspension is dried (Na2SO4)
  2. filtrationfiltered through celite
  3. concentrationAfter concentration under reduced pressure
  4. customthe white solid (34.0 g) is crystallized from EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-8e64fb0de175486682f4ed35ca9f9ed1
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858613B2

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