Triphenylphosphine → 3-[2-(4-(2-Methyl-1,3-dioxolan-2-ylmethoxy)phenoxy)ethyl]-5-(phenoxymethyl)oxazolidin-2-one

Participants

Reaction Steps

Diethyl azodicarboxylate (1.6 ml) was added dropwise to an ice-bath cooled, stirred, solution of 4-[(2-methyl-1,3-dioxolan-2-yl)methoxy]phenol (2.1 g), 5-phenoxymethyl-3-(2-hydroxyethyl)-oxazolidin-2-one (2.4 g) and triphenylphosphine (2.6 g) in anhydrous tetrahydrofuran (50 ml) under argon. The reaction mixture was left for 64 hours at 22° C. and then the solvent removed under reduced pressure. The residue was dissolved in dichloromethane and the solution seeded with 1,2-dicarbethoxyhydrazine. The solution was allowed to stand for 2 hours, the solid was collected and the filtrate was subjected to chromatography using 45% hexane in ethyl acetate grading to 40% hexane in ethyl acetate as eluent. The appropriate fractions were combined, evaporated, and the residue triturated with cyclohexane to give the 3-[2-(4-(2-methyl-1,3-dioxolan-2-ylmethoxy)phenoxy)ethyl]-5-(phenoxymethyl)oxazolidin-2-one (2.7 g) m.p. 75°-77° C.

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