Chlorotrimethylsilane → N-allyl-3-trimethylsilylpropiolic amide

Participants

Reaction Conditions

Reaction Steps

Preferred solvents include ethereals such as THF, diethoxymethane and t-butylmethyl ether. At about 0° C., a strong base is added dropwise over a period of about 15 minutes. Examples of strong bases are n-butyl lithium and lithium diisopropyl amide. While still maintaining the temperature near 0° C., a solution of allyl isocyanate in solvent is added dropwise over about 15 minutes. This is followed by the dropwise addition of trimethylsilyl chloride. After holding the reaction mixture at about 0 to about 10° C. for about 3 hours, the reaction is quenched with aqueous ammonium chloride and extracted with dichloromethane. The solvent is evaporated to yield the product, N-allyl-3-trimethylsilylpropiolic amide. ##STR8## wherein TMS is trimethylsilyl, the solvents are methylene chloride or DCE (1,2-dichloroethane), and the acid catalysts are aluminum chloride (AlCl3), ferric chloride (FeCl3) or methanesulfonic acid (MeSO3).

Provenance & Evidence