Réaction #161127

Équation de réaction

sodium borohydride

1-(1-benzenesulfonyl-2,3-dihydro-1H-indol-5-yl)-ethanone

sodium hydroxide

→

1-benzenesulfonyl-5-ethyl-2,3-dihydro-1H-indole

Rendement 43.4%

Solvants

H2O

TFA

TFA

Conditions de réaction

Traitement

1. 1
   AutreThe organic layer was separated
2. 2
   Extractionthe aqueous layer was extracted with CH2Cl2
3. 3
   LavageThe combined organic layers were washed with brine
4. 4
   Séchagedried over Na2SO4
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   AutreThe residue was purified by column chromatography on silica gel

Mode opératoire

To magnetically stirred TFA (1600 mL) was added at 0° C. sodium borohydride (64 g, 1.69 mol) over 1 h. To this mixture was added dropwise a solution of 1-(1-benzenesulfonyl-2,3-dihydro-1H-indol-5-yl)-ethanone (40 g, 0.13 mol) in TFA (700 mL) over 1 h. The mixture was stirred overnight at 25° C., diluted with H2O (1600 ml), and basified with sodium hydroxide pellets at 0° C. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 1-benzenesulfonyl-5-ethyl-2,3-dihydro-1H-indole (16.2 g, 43%).

Source