Reaktion #7517

Reaktionsgleichung

lithium aluminum hydride

(RS)-indoline-2-carboxylic acid

ethanol

hydrochloric acid

→

title compound

Ausbeute 64.3%

(RS)-2-hydroxymethylindoline

Ausbeute 64.3%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred under ice-
2. 2
   Temperaturcooling
3. 3
   FiltrationThe precipitate was filtered off
4. 4
   Waschenthe mother liquor was washed with saturated brine
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   SonstigeThe solvent was evaporated under reduced pressure
7. 7
   Wascheneluted with ethyl acetate-hexane (1:4-1:1)

Vorschrift

To a solution of (RS)-indoline-2-carboxylic acid (8.16 g, 50 mmol) in tetrahydrofuran (50 ml) was added under ice-cooling lithium aluminum hydride (5.7 g, 150 mmol) and the mixture was stirred at 60° C. for 18 h. The reaction mixture was stirred under ice-cooling and ethanol and 1N hydrochloric acid were added. The precipitate was filtered off and the mother liquor was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was applied to silica gel column chromatography and eluted with ethyl acetate-hexane (1:4-1:1) to give the title compound (4.8 g, 64%).

Quelle