Sodium hydride → Ethyl 3-(5-hydroxy-1-methyl-1H-indol-3-yl)-2-isopropoxypropionate

Participants

Reaction Steps

3.2 g of Ethyl 2-(diethylphosphoryl)-2-isopropylacetate was dissolved in 25 ml of tetrahydrofuran, and 0.44 g of 60% sodium hydride was added under ice-cooling, and stirring was continued for 20 minutes under ice-cooling. The reaction solution was treated with a solution of 2 g of 5-benzyloxy-1-methyl-1H-indol-3-aldehyde in 5 ml of tetrahydrofuran and 5 ml of N,N-dimethylformamide, and stirred at 50° C. for one hour and then at room temperature for 16 hours. The reaction solution was cooled with ice, treated with water and ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and evaporated. The residue was subjected to silica gel column chromatography, and the fraction eluting with 20% ethylacetate-hexane was evaporated and the residue was dissolved in 10 ml of ethanol. 0.6 g of 10% Palladium carbon was added to this solution, the atmosphere was replaced with hydrogen, and the mixture was stirred at room temperature for 24 hours. The reaction atmosphere was replaced with nitrogen, the catalyst was filtered off, and the solvent was evaporated. The residue was subjected to silica gel column chromatography (30% ethyl acetate hexane), to give 2 g of the title compound.

Provenance & Evidence