Imidazole → (2S)-3-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-2-methylpropanoic Acid Methyl Ester

Participants

Reaction Steps

Methyl (S)-(+)-3-hydroxy-2-methylpropionate (1.06 g; 8.99 mmol) (Aldrich) was dissolved in dichloromethane (10 mL, dried over molecular sieves). Imidazole (0.85 g; 12.41 mmol) (Aldrich) and tert-butyl-diphenylsilyl chloride (2.30 mL; 8.85 mmol) (Aldrich) were added and the mixture was stirred at ambient temperature for 3 hours. The reaction was diluted with additional dichloromethane, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to yield methyl (S)-(+)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionate as an oil. (Yield 3.17 g; 98.8%).

Provenance & Evidence