General procedure for the synthesis of (±)-1-phenyl-2-propyn-1-ol acetate and compounds (CAS:84681-19-6) and compounds (CAS:116119-86-9) from vinyl acetate and (±)-1-phenyl-2-propyn-1-ol: The general procedure for kinetic splitting (KR) of ethynyl alcohol is as follows: in a 5 mL drying vial containing lipase PS-30 ( 50 mg, corresponding to 1 mmol of racemic propargyl alcohol) in a 5 mL drying vial, 4A molecular sieves (2 grains) were added and flushed several times with nitrogen. Subsequently, racemic ethynyl alcohol dissolved in anhydrous toluene (2 mL) and vinyl acetate (130 mg, 1.5 mmol) dissolved in anhydrous toluene (4 mL) were added to the vial. The reaction mixture was stirred at 25 °C and the progress of the reaction was monitored by thin-layer chromatography (TLC) [unfolding agent was petroleum ether/ethyl acetate (20:1 to 3:1)] until the raw materials were consumed by about 50%. Upon completion of the reaction, the mixture was filtered and the solids were washed with anhydrous dichloromethane (DCM, 5 mL). Finally, the solvent was removed by vacuum evaporation and the residue was purified by silica gel column chromatography using petroleum ether/ethyl acetate as eluent.
