Water → HCID 54045711, compound

Participants

Reaction Steps

A suspension of 0.26 g of sodium hydride dispersion in 35 ml of tetrahydrofuran was treated with 0.95 g of 5-fluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 1 ml of (S)-methyloxirane the reaction mixture was stirred at room temperature for 48 hours and subsequently treated with 7 ml of water. The mixture was diluted with 180 ml of ether, washed twice with 90 ml of water each time and with 50 ml of saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 28 g of silica gel with toluene-ethyl acetate (19:1). There were obtained 1.15 g (84%) of (S)-1-(5-fluoro-indol-1-yl)-propan-2-ol as a light brown oil.

Provenance & Evidence