Triphenylphosphine → HCID 22107146, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of the compound prepared as described in Example 4 (0.800 g), triphenylphosphine (1.450 g), and 2-hydroxydibenzofuran(1.019 g) intetrahydrofuran (7.0 ml) was cooled to approximately 2° C., and treated with a solution of diethylazodicarboxylate (0.963 g) in tetrahydrofuran (2.0 ml) over a two minute period. After the addition was complete, the reaction was allowed to warm to room temperature. After about 15.5 hours, the solution was concentrated in vacuo. The residue was diluted with toluene (5 ml), the insoluble material removed by filtration, and the filtrate concentrated is vacuo. The oil was dissolved in ethyl acetate and purified by preparative centrifugal thin-layer chromatography (4 mm plate, flow rate=8 ml/min), eluting with ethyl acetate/hexane (1:1) until first band elutes then solvent switched to hexane:ethyl acetate (1:3). The fractions containing the title compound were combined, dried over magnesium sulfate, filtered and concentrated in vacuo to give methyl 3-(2-dibenzofuranoxy)-2-pyrrolidone-5-carboxylate (427 mg). This material contains triphenylphosphine oxide as an impurity.

Provenance & Evidence