Water → 1-(4-Fluorophenyl)-5-hydoxymethyl-1H-indole

HRID 394585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 394585
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17](O)=[O:18])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH2:17][OH:18])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 226030711-(4-Fluorophenyl)-1h-indole-5-carboxylic acid

Produkt 1

HCID 699825031-(4-Fluorophenyl)-5-hydoxymethyl-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of the crude 1-(4-fluorophenyl)-1H-indole-5-carboxylic acid in tetrahydro-furan (700 mL) was added cautiously to a mixture of lithium aluminum hydride (9.8 g) in tetrahydrofuran (400 mL) at 0° C. The resulting mixture was boiled under reflux for 2 h. After cooling to 0° C., water (10 mL), 14% aqueous sodium hydroxide (10 mL) and water (10 mL) was added. Filtration using celite and evaporation of the solvents afforded crystalline title compound 10a (27 g): Mp 69-70° C.; 1H NMR (CDCl3) δ 1.85-1.95 (broad s, 1H), 4.75 (s, 2H), 6.65 (d, 1H), 7.15-7.25 (m, 3H), 7.25 (d, 1H), 7.35-7.45 (m, 3H), 7.65 (broad s, 1H).

Aufarbeitung

  1. temperatureunder reflux for 2 h
  2. filtrationFiltration
  3. customcelite and evaporation of the solvents

Quellen und Nachweise

ORD-Eintrag
ord-87af4212025241e1818a3da29579eb6f
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06602889B1

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