Hydrochloric Acid → HCID 12048064, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-3-indol-2-yl-propane-1,2-diol (S)-1 (15 g, 78.5 mmol) in dry pyridine (120 mL) was added p-toluenesulfonyl chloride (15.5 g, 81.3 mmol) at 0° C. After stirring for 5 hours at 0° C., the solution was poured into cold hydrochloric acid (100 mL, 6N) and extracted with ether (3×60 mL). The combined extracts were washed with hydrochloric acid (6N, 2×30 mL) followed by brine (2×80 mL) and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by flash chromatography to give 24.5 g (90.4%) of the title compound as a white solid.

Provenance & Evidence