Triethylamine → 3-[(E)-3-naphthalen-2-ylprop-2-enoyl]-1,3-oxazolidin-2-one

Participants

Reaction Steps

To a stirred solution of (E)-3-(2-naphthyl)prop-2-enoic acid (10 g, 0.05 mole) at −78° C., was added triethylamine (8.42 ml, 0.06 mole) and pivaloyl chloride (7.5 ml, 0.06 mole). Stirring was continued for 1 hour. To a stirred solution of oxazolidinone (5.14 g, 0.06 mole) in dry tetrahydrofuran (200 ml) at −78° C. was added slowly n-butyl lithium (1.6M in hexanes, 38 ml, 0.06 mole). Stirred for 1 hour. The suspension of the mixed anhydride was transferred into the oxazolidinone anion by means of a canula maintaining the temperature below −60° C. The resulting reaction mixture was stirred for 2 hours. Water was added cautiously and the reaction extracted with ethyl acetate. The solvent was washed with brine, dried and evaporated to dryness in-vacuo. Chromatography on flash silica using ethyl acetatehexane (1:1) gave 3-[(E)-3-naphthalen-2-ylprop-2-enoyl]-1,3-oxazolidin-2-one as a white solid, M/e 268 (M+H).

Provenance & Evidence