Triethylamine → Propanoic acid, 2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, (2S)-

Participants

Reaction Steps

A solution of t-butylchlorodiphenylsilane, TBDPSCl, (7.9 g, 28.9 mmoL) in THF (20 mL) was slowly added via canula into a solution of triethylamine (7.4 mL, 53.1 mmol), DMAP(catalytic amount) and L-(+)-lactic acid 9 (2.0954 g, 26.16 mmol) in THF (20 mL) and dichloromethane (20 mL) at room temperature. The resulting mixture, a white suspension, was stirred at room temperature for 2 days. The reaction mixture was washed sequentially with water, 3N HCl and water, dried over Na2SO4, filtered and solvent was removed under vacuum. The product was purified by column chromatography on silica using EtOAc/hexane=1/3 and 1/1 as eluent to obtain 4.965 g (58%) of 10.

Provenance & Evidence