Water → Methyl 4-[(phenylmethylene)amino]-6-(trimethylsilyl)-5-hexynoate

Participants

Reaction Conditions

Reaction Steps

53.6 ml of a 1.6M solution of n-butyllithium in hexane was added drop-by-drop over 20 minutes to a solution of 18.0 g of 1B in 700 ml of dry tetrahydrofuran at -70° C. The resulting mixture was stirred for 20 minutes at -70° C., when 7.2 g of freshly distilled methyl acrylate was added over 14 minutes. The resulting mixture was stirred for 30 minutes at -70° C., when 16.5 ml of water was added drop-by-drop. The resulting mixture was allowed to warm slowly to room temperature; the solvent was evaporated; the residue was diluted with water and the resulting mixture was extracted with ether. The ether extract was washed with brine, dried (Na2SO4), filtered and the solvent was evaporated. The residue (a dark thick oil) was distilled in a Kugelrohr apparatus to give methyl 6-(trimethylsilyl)-4-(benzylideneamino)-5-hexynoate (3A), b.p.: 140°-142° C. (0.01 Torr.).

Provenance & Evidence