Réaction #439112

Équation de réaction

ethyl 3-phenyl-3-(6-hydroxyindol-3-yl)propionate

Ethyl 3-phenyl-3-(6-hydroxyindol-3-yl)propionate

tert-butyl bromoacetate

potassium carbonate

toluene acetone

→

ethyl 3-phenyl-3-[6-(tert-butoxycarbonylmethoxy)indol-3-yl]propionate

Solvants

acetone

Conditions de réaction

Traitement

1. 1
   Filtrationthe residue is filtered off
2. 2
   Autrethe solution is evaporated
3. 3
   Autrethe crude product is purified by chromatography on silica gel (eluent toluene/acetone 9:1)

Mode opératoire

The compound ethyl 3-phenyl-3-(6-hydroxyindol-3-yl)propionate 4 prepared analogously to Example 1.1-1.3 (3.23 mmol) is stirred overnight at 60° C. with 0.94 ml (6.4 mmol) of tert-butyl bromoacetate and 1.8 g (13 mmol) of potassium carbonate in 20 ml of acetone. When the reaction is complete (TLC check toluene/acetone 4:1), the residue is filtered off, the solution is evaporated, and the crude product is purified by chromatography on silica gel (eluent toluene/acetone 9:1), giving ethyl 3-phenyl-3-[6-(tert-butoxycarbonylmethoxy)indol-3-yl]propionate.

Source