Acetyl chloride → N-[(5-Chloro-2-iodophenyl)methylene]-1-[(trimethylsilyl)oxy]ethenamine

Participants

Reaction Steps

In a manner similar to the method described in example 190b, 5-chloro-2-iodobenzaldehyde prepared in example 208a (3.97 g, 15 mmol) was used as the starting material in place of 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-iodo-benzaldehyde to react with 1,1,3,3,3-hexamethyldisilazane (2.4 g, 15 mmol), n-butyllithium (2.5 M, 6 mL, 15 mmol), trimethylsilyl chloride (1.6 g, 15 mmol), triethylamine (2 g, 20 mmol) and acetyl chloride (1.5 g, 20 mmol) to give crude 1-(5-chloro-2-iodophenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene as a yellow gum and used for the next step without further purification.

Provenance & Evidence