Triphenylphosphine → HCID 22107101, compound

Participants

Reaction Steps

A mixture of the compound prepared as described in Example 4 (3.612 g), triphenylphosphine (6.759 g), and 1-(4-hydroxyphenyl)-6-phenylhexane (6.5555 g) in tetrahydrofuran (32 ml) was cooled to approximately 1-2 C, and treated with a solution of diethylazodicarboxylate (4.080 g) in tetrahydrofuran (10 ml) over a seventeen minute period. After the addition was complete, the reaction suspension was allowed to warm to room temperature. After about 24 hours, the resulting brown solution was concentrated in vacuo. The residue was diluted with chloroform (10 ml), the insoluble material removed by filtration, and the filtrate concentrated in vacuo. The material was dissolved in methylene chloride and 230-400 mesh silica gel (36 g) was added. The mixture was concentrated in vacuo to a powder. The mixture was subjected to flash silica gel chromatography, eluting with hexane/ethyl acetate (5:2, 10×100 ml), then hexane/ethyl acetate (5:3, 7×100 ml, 1×200 ml), next ethyl ether (10×2000 ml) and finally ethyl acetate (2×200 ml, 2×500 ml). The fractions containing the desired material were concentrated in vacuo to give a gold oil. The gold oil was dissolved in methylene chloride (24 ml) and purified by preparative centrifugal thin-layer chromatography (4 mm plate, flow rate=8 ml/min), eluting with 50% ethyl acetate/hexane until the first band elutes then solvent switched to ethyl acetate. The fractions containing methyl 3-(4-(6-hexylphenyl)phenoxy]-2-pyrrolidone-5-carboxylate were combined and concentrated in vacuo to give a gold oil. The oil was dissolved in diethyl ether (10 ml). Hexane was added until the solution became turbid. After forty five minutes at room temperature, the turbid solution was concentrated in vacuo resulting in the formation of a solid material. Diethyl ether (10 ml) was added to the material, then the insolubles were collected by filtration. The filtrate was concentrated in vacuo to give as oil that crystallizes out. Diethyl ether was added to the crystalline material. The resulting suspension was rigorously stirred for thirty minutes. Insolubles were collected by filtration to give 3.91 g of methyl 3-(4-(6-hexylphenyl)phenoxy)-2-pyrrolidone-5-carboxylate.

Provenance & Evidence