Lithium Hexamethyldisilazide → 4(R)-benzyl-3-{2-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-3-methylbutyryl}oxazolidin-2-one

Participants

Reaction Steps

A solution of 0.31 g of 4(R)-benzyl-3-(3-methylbutyryl)oxazolidin-2-one in 2 ml of tetrahydrofuran is added dropwise at −78° C. to 1.2 ml of lithium bis(trimethylsilyl)amide solution (1M in tetrahydrofuran). After 30 minutes, a solution of 0.30 g of 7-bromomethyl-1-(2-methoxyethoxy)naphthalene in 2 ml of tetrahydrofuran is added dropwise and the reaction mixture is allowed to thaw from −78° C. to 0° C. over 2 hours. After 3 hours at 0° C., the reaction mixture is quenched with 5 ml of 1M ammonium chloride solution, diluted with water and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with brine, dried over sodium sulphate and concentrated by evaporation. The title compound is identified on the basis of the Rf value from the residue by means of flash chromatography (SiO2 60F).

Provenance & Evidence