Benzene → (R)-4-(6-Methoxynaphthalen-2-yl)-4-methyloxazolidin-2-one

Participants

Reaction Steps

A mixture of carbamic acid (S)-2-(6-methoxy-naphthalen-2-yl)-propyl ester (5.4 g, 0.0208253 mol), iodobenzene diacetate (9.46 g, 0.0294 mol; Acros) and magnesium monoxide (1.93 g, 0.0479 mol; Aldrich), and rhodium(II) acetate dimer (500 mg, 0.001 mol; Janssen) in benzene (250 mL, 2.8 mol; Aldrich) was refluxed overnight under N2. TLC (EtOAc-hexanes 2:3) showed a slow moving spot. The solution was diluted with EtOAc and filtered through CELITE™ and washed with EtOAc and MeOH. Silica gel was added to the solution, which was then concentrated and purified on a 120 g silica gel column with 10-50% EtOAc/hexanes to give precipitate.

Provenance & Evidence