Chlorotrimethylsilane → 2,2-Dimethyl-3-trimethylsilanyloxy-propionic acid methyl ester

Participants

Reaction Steps

TMSCl (2.30 mL, 0.018 mol) was added dropwise to a solution of 3-hydroxy-2,2-dimethyl-propionic acid methyl ester (2.0 g, 0.015 mot) and triethylamine (3.16 mL, 0.023 mol) in dichloromethane at 0° C. After stirring for 1 h, the reaction was warmed to room temperature and stirred for an additional 1.5 h. Volatiles were removed under reduced pressure to provide a solid that was slurried in a mixture of ethyl ether and hexanes. The solid was removed by filtration and the filtrate was concentrated to provide a yellow liquid that was purified by bulb to bulb distillation under reduced pressure to provide 2,2-dimethyl-3-trimethylsilanyloxy-propionic acid methyl ester (2.8 g, 91%) as a colorless liquid.

Provenance & Evidence