tert-Butyl methyl ether → HCID 86633033, compound

Participants

Reaction Steps

A mixture of 33 mL methyl-tert-butyl ether (MTBE) and 0.33 mL water was stirred until a clear solution was obtained (ca. 5 hrs). To this solution was added methylthiocarbonyloxybutyl butanoate (2e) (2.0 g) and PLE/MPEG (60 mg/1 g; 12.65 g). The resulting suspension was stirred at room temperature. The reaction was monitored by 1H-NMR using a chiral solvating agent. After ca. 5 days, the reaction was quenched by filtration through a pad of CELITE® 545. The supernatant was washed with water, aqueous sodium bicarbonate (NaHCO3) and brine, and dried over anhydrous sodium sulfate (Na2SO4). Evaporation of the solvent afforded 0.20 g (20% yield) of the title compound (16). The enantiomeric excess as determined by chiral HPLC was 90% e.e.

Provenance & Evidence