Chloride → N,N-bis-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-chloro-acetamide

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Reaction Steps

Choloroacetyl chloride (1.1 g, 9.55 mmol) and potassium carbonate (2.638 g, 19.09 mmol) were dissolved in dry dichloromethane (80 mL) and cooled in an ice salt bath. To this was added bis-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]amine (3.353 g, 9.545 mmol) in dry dichloromethane (10 mL) over 10 minutes. The reaction mixture was stirred in an ice bath for 2 hours. The mixture was filtered and washed with dichloromethane, then washed with 1.5 N aqueous potassium hydrogen sulfate (2×100 mL) and brine (100 mL). The aqueous layers were back extracted with dichloromethane (2×100 mL), dried over sodium sulfate, filtered and concentrated in vacuo to give N,N-bis-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-chloro-acetamide (3.8 g, 87.4%).

Provenance & Evidence