Chlorotrimethylsilane → HCID 87437838, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, 5.25 g (0.05 moles) of aminoacetaldehyde dimethylacetal were dissolved in 50 ml of dry tetrahydrofuran and cooled to −78° C. 20 ml of 2.5M nBuLi (0.05 moles) were then added over 5 minutes with stirring. The mixture was then stirred for 15 minutes at −78 C then allowed to slowly warm to room temperature. 6.3 ml (0.05 moles) of chlorotrimethylsilane were then added over 20 minutes and the reaction allowed to stir for an additional 30 minutes. During this addition the mixture increased in temperature and a precipitate of lithium chloride was observed to form. The mixture was then cooled back down to −78 C and an additional 20 ml of 2.5M nBuLi added over 5 minutes with stirring and the mixture was held at this temperature for an additional 15 minutes before being allowed to warm back up to room temperature. An additional 6.3 ml of chlorotrimethylsilane was then added over a 20 minute period with stirring, during which time the mixture was observed to warm up and additional lithium chloride form. The Mixture was then stirred for an additional 30 minutes before being filtered. The tetrahydrofuran was then removed from the filtrate by vacuum and the final product was vacuum distilled from the remaining filtrate. This resulted in a yield of 8.0 g (64% of theoretical) of (Me3Si)2NCH2CH(OMe)2.

Provenance & Evidence