2-Naphthaleneacetic acid → 2-(2-Naphthyl)acetyl chloride

Participants

Reaction Steps

To a stirred solution of 2-naphthylacetic acid (0.960 g, 5.15 mmol) in methylene chloride (10 mL) was added oxalyl chloride (0.58 mL, 6.7 mmol) and DMF (1 drop). After 1.5 hours, the solvent was evaporated to give 2-naphthylacetyl chloride. A solution of the 2-naphthylacetyl chloride in THF (3 mL), cooled to −78° C., was slowly cannulated into a stirred solution of the lithium salt of 4-(S)-(+)-4-isopropyl-2-oxazolidinone (prepared by treating, at −78° C., a solution of 4-(S)-(+)-4-isopropyl-2-oxazolidinone (0.60 g, 5.2 mmol) in THF (4 mL) with a solution of butyllithium (1.6 M in hexane) for 15 min). After 2 hours, 10% citric acid and ethyl acetate were added. The organic phase was washed with NaHCO3 and brine, dried (MgSO4), and concentrated. Flash column chromatography of the residue (15% ethyl acetate/hexanes) gave 4-(S)-4-isopropyl-3-(2-naphthylacetyl)-2-oxazolidinone as a slightly yellow oil (0.91 g, 60%).

Provenance & Evidence