Reaktion #468501

Reaktionsgleichung

6-methoxycarbonyl-1-methylindole

6-bromo-1-methylindole

diisobutyl aluminium hydride

→

subtitle compound

6-Hydroxymethyl-1-methylindole

Lösungsmittel

tetrahydrofuran

water

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat −70° C.
2. 2
   workup.STIRRINGThe solution was stirred at −70° C. for 15 mins
3. 3
   Sonstigepartitioned between ethyl acetate and aqueous sodium hydroxide
4. 4
   ExtraktionThe aqueous layer was re-extracted with ethyl acetate
5. 5
   Trocknenwere dried (MgSO4)
6. 6
   Sonstigeevaporated
7. 7
   Sonstigeto give crude product which
8. 8
   Sonstigewas purified by flash column chromatography

Vorschrift

To a solution of 6-methoxycarbonyl-1-methylindole (prepared by the method of Example 1(b), but using 6-bromo-1-methylindole in place of 6-bromo-1-ethylindole, 5g) in tetrahydrofuran (30 ml) at −70° C. under a nitrogen atmosphere, was added diisobutyl aluminium hydride (66 ml of a 1.0M solution in tetrahydrofuran) dropwise with stirring. The solution was stirred at −70° C. for 15 mins then warmed to room temperature for 2 hours. The mixture was diluted with water (100 ml) and partitioned between ethyl acetate and aqueous sodium hydroxide. The aqueous layer was re-extracted with ethyl acetate and combined organic extracts were dried (MgSO4) and evaporated to give crude product which was purified by flash column chromatography using 80% ethyl acetate/20% hexane eluant to give the subtitle compound as a clear oil which solidified on standing (4.1 g).

Quelle