Methyl iodide → ethyl 2-(trimethylsilyl)propanoate

Participants

Reaction Steps

To a solution of 21.8 mL (0.156 mole) of diisopropylamine in 100 mL of THF at 0° was added 0.156 mole of butyl lithium/hexane. After 30 minutes at 0°, the solution was cooled to -78°, and 25 g (0.156 mole) of ethyl trimethylsilylacetate was added. After 30 minutes at -78°, 22.7 g (10 mL, 0.16 mole) of methyl iodide was added. After warming to room temperature, the mixture was filtered, and the filtrate was evaporated. The residue was treated with hexane and filtered under argon The hexane layer of the filtrate was concentrated and distilled in a small Vigreux column to give 12 g of ethyl 2-trimethylsilylpropionate, b.p. 61.4°/15 mm.

Provenance & Evidence