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-butyldiphenylsilyl chloride (2.30 mL, 8.85 mmol) (Aldrich) were added and the mixture was stirred at ambient temperature for three hours. The reaction was diluted with additional dichloromethane, washed with water and brine, dried over anhydrous sodium sulfate 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